Water → 4-Cyano-5-methyl-4-(3-thienyl)hexanol

HRID 1071636Notes

Reaction equation

HRID 1071636 reaction equation
O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].O.[C:15]([C:17]([C:28]1[CH:32]=[CH:31][S:30][CH:29]=1)([CH:25]([CH3:27])[CH3:26])[CH2:18][CH2:19][C:20](OCC)=[O:21])#[N:16]>>[C:15]([C:17]([C:28]1[CH:32]=[CH:31][S:30][CH:29]=1)([CH:25]([CH3:27])[CH3:26])[CH2:18][CH2:19][CH2:20][OH:21])#[N:16]

Participants

6

Reactant 5

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22393748Ethyl 4-cyano-5-methyl-4-(3-thienyl)hexanoate

Product 1

HCID 223937214-Cyano-5-methyl-4-(3-thienyl)hexanolYield 95%

Procedure

A tetrahydrofuran solution (35 ml) in which ethyl 4-cyano-5-methyl-4-(3-thienyl)hexanoate (6.66 g) was dissolved was added dropwise to a tetrahydrofuran solution (50 ml) of lithium aluminum hydride (686 mg). After stirring for 2 hours, 2N aqueous NaOH and water were added to treat the mixture, and the resulting precipitates were filtered. The resulting filtrate was evaporated, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a yellow oil (5.30 g, 95%).

Workup

  1. additionto treat the mixture
  2. customthe resulting precipitates
  3. filtrationwere filtered
  4. customThe resulting filtrate was evaporated
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-329c02ab1fd942cdb911f787f77129d2
Source dataset
uspto-grants-2005_06
Patent number
US06906072B1

Reaction notes

Loading…