Diethyl Ether → HCID 20352315, compound

HRID 371954Notes

Reaction equation

HRID 371954 reaction equation
[CH3:1][CH:2]([CH:9]=[C:10]=[C:11]([CH3:18])[CH2:12][CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])[CH2:3]C(OCC)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].CC[O:27]CC>>[CH3:1][CH:2]([CH:9]=[C:10]=[C:11]([CH3:18])[CH2:12][CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])[CH2:3][OH:27]

Participants

4

Reactant 3

HCID 3283Diethyl Ether2×HCID 20352318HCID 20352318, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20352315HCID 20352315, compoundYield 77%

Procedure

A solution of 25 mM of the ester obtained according to letter (i) above in 13 ml of anhydrous ether was added under stirring to a solution of 0.66 (17.5 mM) of LiAlH4 in 35 ml of anhydrous ether. Stirring was carried on at room temperature for 22 h, whereupon the reaction mixture was poured onto ice. After acidification with a 10% aqueous HCl solution, extraction with ether, washing with water and drying, followed by evaporation and distillation there was obtained a fraction having b.p. 130°-7°/12 Torr (yield 77%) containing 90-95% of the desired allenic alcohol in the form of a diastereoisomeric mixture.

Workup

  1. additionwas added
  2. additionwas poured onto ice
  3. extractionAfter acidification with a 10% aqueous HCl solution, extraction with ether
  4. washwashing with water
  5. customdrying
  6. customfollowed by evaporation
  7. distillationdistillation there
  8. customwas obtained a fraction

Sources & evidence

ORD record
ord-186793b2794341adbd4afa15d8cbcfb7
Source dataset
uspto-grants-1978_05
Patent number
US04088664

Reaction notes

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