Reduction of Some Enolizable β-Dicarbonyl Compounds to Unsaturated Alcohols by Lithium Aluminum Hydride. I. Monocyclic β-Ketoesters and α-Hydroxymethylene Ketones1

1953 ◽  
Vol 75 (4) ◽  
pp. 939-943 ◽  
Author(s):  
Andre S. Dreiding ◽  
John A. Hartman
Keyword(s):  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Lithium Aluminum ◽  
Dicarbonyl Compounds ◽  
Unsaturated Alcohols

Synthesis of some unsaturated 19a-homocholestane derivatives

1983 ◽  
Vol 48 (12) ◽  
pp. 3597-3605 ◽  
Author(s):  
Pavel Kočovský
Keyword(s):  
Lithium Aluminum Hydride ◽  
Methanesulfonic Acid ◽  
Aluminum Hydride ◽  
Cyclic Ether ◽  
Lithium Aluminum ◽  
Unsaturated Alcohols ◽  
Hypobromous Acid ◽  
Zinc Reduction

A synthesis of unsaturated alcohols I, IV-VI is described. The 3,4-unsaturated derivative I was prepared in three steps from the mesylate VIII which by elimination of methanesulfonic acid afforded a mixture of olefins IX yielding two bromo epoxides XII and XIII on treatment with hypobromous acid. Zinc reduction of the compound XIII gave the hydroxy olefin I. In the synthesis of the derivative IV inversion of configuration at C(3) (formally II → IV) was performed in the following manner: reaction of the hypobromous acid with III gave the cyclic ether XV which after saponification and oxidation was converted into the ketone XVIII and the latter was reduced with lithium aluminum hydride to yield a mixture with prepondering equatorial alcohol XX. This compound was acetylated and reduced with zinc to give IV. The 3-epimeric 10β-vinylalcohols V and VI were obtained by reduction of the ketone XXVII.

The Preparation of Specifically Deuterated trans- Cinnamyl Alcohol and trans- Cinnamic Acid

1973 ◽  
Vol 51 (13) ◽  
pp. 2102-2104 ◽  
Author(s):  
Donald G. Lee ◽  
James R. Brownridge
Keyword(s):  
Cinnamic Acid ◽  
Triple Bond ◽  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Lithium Aluminum ◽  
Cinnamyl Alcohol ◽  
Partial Reduction ◽  
Work Up

The reduction of ethyl phenylpropiolate by lithium aluminum hydride results in partial reduction of the triple bond to give trans-cinnamyl alcohol. If ethyl phenylpropiolate is reduced by LiAlD4 followed by work-up with acetone and H2O the product is the specifically labeled compound, trans-3-phenyl-2-propen-1-ol-1,1,2-d3. If the ester is reduced with LiAlH4 followed by work-up with acetone-d6 and D2O the product is trans-3-phenyl-2-propen-1-ol-O,3-d2. Oxidation of these two products by sodium ruthenate leads to formation of trans-cinnamic acid-α-d and trans-cinnamic acid-β-d, respectively.

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