Behaviour of 2′-O-p-toluenesulfonyl uridine towards excess of a Grignard reagent

1989 ◽  
Vol 67 (4) ◽  
pp. 708-709 ◽  
Author(s):  
Annie Grouiller ◽  
Hassan Essadiq
Keyword(s):  
Grignard Reagent ◽  
Grignard Reaction ◽  
Methylmagnesium Iodide

Two C-methylated base nucleosides were obtained when 2′-O-tosyl-5′-O-trityluridine was reacted with 30 equivalents of methylmagnesium iodide. Keywords: nucleoside, Grignard reaction, C-methyl pyrimidinone, anhydro derivative, arabinofuranosyl.

Synthesis of 1,1,5,6-Tetramethyl- and 7-Isopropyl-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene

1999 ◽  
Vol 64 (3) ◽  
pp. 527-532 ◽  
Author(s):  
Ramchandra Bhimrao Mane ◽  
Abhijit Jaysingrao Kadam ◽  
Rajashree Sandeep Salunkhe
Keyword(s):  
Trifluoroacetic Acid ◽  
Polyphosphoric Acid ◽  
Titanium Tetrachloride ◽  
Grignard Reaction ◽  
Butanoic Acid ◽  
Methylmagnesium Iodide

4-(2,3-Dimethylphenyl)butanoic acid (4) was treated with excess of methyllithium to yield 5-(2,3-dimethylphenyl)-2-methylpentan-2-ol (6) which was cyclodehydrated using Dowex 50W-X8 resin, trifluoroacetic acid or polyphosphoric acid (PPA) to furnish 1,1,5,6-tetramethyl-1,2,3,4-tetrahydronaphthalene (1). The acid 4 was cyclized with PPA to furnish 5,6-dimethyl-3,4-dihydronaphthalen-1(2H)-one (5) which was converted into 1 by reaction with dimethylzinc and titanium tetrachloride. 4-(4-Isopropylphenyl)butanoic acid (7) on esterification followed by Grignard reaction with methylmagnesium iodide furnished 5-(4-isopropylphenyl)-2-methylpentan-2-ol (9), which was cyclodehydrated as above to yield 7-isopropyl-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene (2).

scholarly journals SINTESIS FEROMON 6-METIL-2-HEPTEN-4-OL DARI KROTONALDEHID MELALUI PEMBENTUKAN REAGEN GRIGNARD ISOBUTILMAGNESIUM BROMIDA

2010 ◽  
Vol 5 (2) ◽  
Author(s):  
Putu Indrayani ◽  
Aliefman Hakim
Keyword(s):  
Grignard Reagent ◽  
Refraction Index ◽  
Magnesium Bromide ◽  
Grignard Reaction ◽  
Stretching Vibration ◽  
Nh4cl Solution

Abstrak : Sintesis 6-metil-2-hepten-4-ol diawali dengan pembentukan reagen Grignard isobutilmagnesium bromida pada 400C selama 1 jam, dilanjutkan dengan pembentukan garam alkoksi magnesium bromida pada 00C.Hidrolisis terhadap garam alkoksi magnesium bromida dengan larutan NH4Cl jenuh menghasilkan 6-metil-2-hepten-4-ol. Hasil sintesis kemudian diuji sifat fisiko-kimianya meliputi berat jenis, indeks bias serta identifikasi denganSpektrofotometer Inframerah (IR), Kromatografi Gas (GC) dan Kromatografi Gas-Spektrometer Massa (GC-MS). Hasil sintesis menghasilkan cairan beraroma manis segar, berwarna kekuningan, berat jenis 0,81529 g/mL, indeks bias 1,40830, kemurnian 66,07 % dan hasil 46,31 %. Karakter IR senyawa hasil sintesis menunjukkan vibrasi ulur O-H alkohol pada 3361 cm-1, vibrasi ulur C-OH pada 1049,2 cm-1, vibrasi ulur C=C pada 1676 cm-1 dan serapan 2956,7 dan 2920 cm-1 untuk vibrasi ulur C-H dalam CH 3 dan spektra massa dengan m/e 128 yang dicapai pada waktu retensi 6,284 menit. Data-data tersebut mendukung bahwa senyawa hasil sintesis adalah 6-metil-2-hepten-4-ol.Kata kunci : Sintesis, reaksi Grignard dan 6-metil-2-hepten-4-olAbstract : Synthesis of 6-methyl-2-hepten-4-ol was generated with formation of Grignard reagent Isobutylmagnesium bromide carried out at 400C for one hour, then formation of alcoxide salt magnesium bromide carried out at 00C. Alcoxide salt magnesium bromide were hydrolyzed by saturated NH4Cl solution producing 6-methyl-2-hepten-4-ol. Results were examined physically and chemically including density, refraction index, pure percentage and yield percentage were 0,81529 g/mL, 1,40830, 66,07 % and 46,31 % respectively. The IR characters showed stretching vibration of O-H group at 3361 cm-1, stretching vibration C-OH group at 1049,2 cm-1, stretching vibration C=C group at 1676 cm-1 and absorption of C-H in CH3 2956,7 and 2920 cm-1. Identification using GC-MS resulted spectra m/e 128 at time retention 6,284 minutes. The proven data indicated that the resulted compound was 6-methyl-2-hepten-4-ol.Keywords : synthesis, Grignard reaction and 6-methyl-2-hepten-4-ol

Hyperbranched Conductive Polymers Constituted of Triphenylamine

1999 ◽  
Vol 600 ◽  
Author(s):  
S. Tanaka ◽  
K. Takeuchi ◽  
M. Asai ◽  
T. Iso ◽  
M. Ueda
Keyword(s):  
Molecular Weight ◽  
Conjugated Polymer ◽  
Grignard Reagent ◽  
Average Molecular Weight ◽  
Catalytic Amount ◽  
Oxidation Potential ◽  
Grignard Reaction ◽  
Step Process ◽  
One Step ◽  
Dark Blue

AbstractA hyperbranched conjugated polymer containing triphenylamine was prepared by the Grignard reaction of tris(4-bromophenyl)amine 1, via the coupling of N, N-bis(4-bromophenyl)-N-(4-bromomagnesiophenyl)amine 2 with the catalytic amount of Ni(acac)2. Grignard reagent 2 reacted as an AB2-type monomer to give hyperbranched conjugated polymer 3 in a one-step process. Polymer 3 was also obtained via the Pd-catalyzed coupling of N, N-bis(4-bromophenyl)-4-animobenzeneboronic acid 4. Polymer 3 had an average molecular weight of 4.0–6.3×103 and was found to be soluble in organic solvents such as THF and CHC13. A cast film had an anodic peak at 0.95–1.20 V vs. Ag wire. It was dark blue above the oxidation potential and brown-yellow in the neutral state. When polymer 3 was doped with iodine, its conductivity rose to 0.8–3.0 S/cm

Mechanism of Acetal Cleavage with Methylmagnesium Iodide

1985 ◽  
Vol 38 (7) ◽  
pp. 1031
Author(s):  
AD Abell ◽  
RA Massy-Westropp
Keyword(s):  
Grignard Reagent ◽  
Tertiary Alcohol ◽  
Methyl Group ◽  
Methylmagnesium Iodide ◽  
Oxygen Bond

The reaction of methylmagnesium iodide with methyl (1R,3S,5R)-1-(furan- 3′-yl)-5-methyl-2,8-dioxabicyclo[3.2.1]octane-3-carboxylate (2) gives products arising from regioselective carbon-oxygen bond fission and intermolecular transfer of the methyl group of the Grignard reagent to the intermediate oxocarbonium ion, in addition to the usual tertiary alcohol.

Synthesis of the radical scavenger 1,1,3,3-Tetramethylisoindolin-2-yloxyl

1983 ◽  
Vol 36 (2) ◽  
pp. 397 ◽  
Author(s):  
PG Griffiths ◽  
G Moad ◽  
E Rizzardo
Keyword(s):  
Free Radical ◽  
Small Proportion ◽  
Radical Scavenger ◽  
Grignard Reaction ◽  
Radical Trapping ◽  
Methylmagnesium Iodide ◽  
Trapping Agent

A versatile free-radical trapping agent, 1,1,3,3-tetramethylisoindolin-2-yloxyl, has been prepared from N-benzylphthalimide by reaction with 'methylmagnesium iodide' in refluxing toluene followed by hydrogenolysis and oxidation. The Grignard reaction gives 2-benzyl-1,1,3,3-tetramethylisoindoline along with a small proportion of an unexpected by-product, 2-benzyl-1-ethyl-1,3,3-trimethyliso-indoline.

Studies in ferrocene derivatives. VII. The synthesis of ferrocenyl ethylenes via an abnormal Grignard reaction

1969 ◽  
Vol 47 (17) ◽  
pp. 3085-3088 ◽  
Author(s):  
W. H. Horspool ◽  
R. G. Sutherland ◽  
J. R. Sutton
Keyword(s):  
Grignard Reagent ◽  
Acid Strength ◽  
Nucleophilic Attack ◽  
Grignard Reaction ◽  
Ferrocene Derivatives ◽  
Carbonium Ions ◽  
General Synthesis

RMgBr reacts normally with acylferrocenes to give the corresponding alcohols. RMgI gives good yields of the most highly substituted ferrocenyl ethylene. In solutions of moderate acid strength, α-ferrocenyl carbonium ions lose a proton to form the substituted alkene rather than undergo nucleophilic attack by water to give the corresponding alcohol. Since the alcohols are more basic than the alkenes, it is possible to devise a general synthesis of ferrocenyl ethylenes by the reaction of any Grignard reagent with an acylferrocene.

Construction of the Side-Chain in 14β-Androst-5-ene Derivatives. Preparation of 14β-Pregnenolone

1994 ◽  
Vol 59 (12) ◽  
pp. 2691-2704 ◽  
Author(s):  
Ivan Černý ◽  
Miloš Buděšínský ◽  
Pavel Drašar ◽  
Vladimír Pouzar
Keyword(s):  
Nmr Spectra ◽  
Side Chain ◽  
Grignard Reaction ◽  
Diisobutylaluminum Hydride ◽  
Subsequent Oxidation ◽  
Hydride Reduction ◽  
Methylmagnesium Iodide ◽  
A Minor

Stepwise side-chain construction schemes leading to pregnane derivatives were tested in the 14β-androst-5-ene series. 6β-Methoxy-3α,5-cyclo-5α,14β-androstan-17-one (I) gave after methylenation and hydroboration the 17α-hydroxymethyl derivative III. Subsequent oxidation to the aldehyde VI, Grignard reaction with methylmagnesium iodide, and reoxidation led to the ketone VII and to the isomeric 17β-derivative VIII as a minor product. Final i-steroid cleavage of VII furnished the known 14β,17α-pregnenolone IX; the minor product VIII gave the 17β-isomer X. Alternatively, the ketone X was prepared from 6β-methoxy-3α,5-cyclo-5α,14β-androstan-17α-ol p-toluenesulfonate (XI) by cyanide substitution, diisobutylaluminum hydride reduction to the aldehyde XIV, and further as described for IX. The mass and NMR spectra of the four pregnenolone derivatives IX, X, XVIII, and XIX, isomeric in positions 14 and 17, were studied.

Study on Synthesis of 2-Hydroxy-6-Naphthoic Acid from 2-Naphthol and Improve the Synthetic Process

2013 ◽  
Vol 634-638 ◽  
pp. 2044-2048
Author(s):  
Yang Wang ◽  
Qiang Li ◽  
Xian Feng Gong ◽  
Xue Ling Zhao ◽  
Yu Zhang
Keyword(s):  
Carbon Dioxide ◽  
Grignard Reagent ◽  
Reducing Agent ◽  
Raw Material ◽  
Grignard Reaction ◽  
Solid Carbon ◽  
Solid Carbon Dioxide ◽  
Synthetic Process ◽  
Naphthoic Acid

2-Hydroxy-6-naphthoic acid is an main raw material for the synthesis of polyaromatic ester, it was synthesized from 2-Naphthol by methoxylation, bromization, grignard reaction and demethylation before recrystallization (C2H5OH:H2O=2.8:1 m/m) with an overall yield of 78.5% and content of 99.1%. Furthermore, the results showed that the 6-bromo-2-methoxynaphthalene was prepared using Sn as reducing agent with 96.2% of the yield which is higher than 6-bromo-2-methoxynaphthalene was prepared using solid carbon dioxide and grignard reagent with 23.8% of the yield.

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