Water → [5-((E)-1,5-diethyl-5-triethylsilanyloxyhept-1-enyl)-3-thienyl]methanol

HRID 49346Notes

Reaction equation

HRID 49346 reaction equation
[CH2:1](/[C:3](/[C:20]1[S:24][CH:23]=[C:22]([CH:25]=[O:26])[CH:21]=1)=[CH:4]\[CH2:5][CH2:6][C:7]([CH2:18][CH3:19])([O:10][Si:11]([CH2:16][CH3:17])([CH2:14][CH3:15])[CH2:12][CH3:13])[CH2:8][CH3:9])[CH3:2].[BH4-].[Na+].O>C1COCC1.CO>[CH2:1](/[C:3](/[C:20]1[S:24][CH:23]=[C:22]([CH2:25][OH:26])[CH:21]=1)=[CH:4]\[CH2:5][CH2:6][C:7]([CH2:8][CH3:9])([O:10][Si:11]([CH2:16][CH3:17])([CH2:12][CH3:13])[CH2:14][CH3:15])[CH2:18][CH3:19])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 867593895-((E)-1,5-diethyl-5-triethylsilanyloxyhept-1-enyl)thiophene-3-carbaldehyde

Product 1

HCID 69825153[5-((E)-1,5-diethyl-5-triethylsilanyloxyhept-1-enyl)-3-thienyl]methanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4 g (9.9 mmol) of 5-((E)-1,5-diethyl-5-triethylsilanyloxyhept-1-enyl)thiophene-3-carbaldehyde are dissolved in 50 mL of THF and 50 mL of methanol. 1 g (26 mmol) of sodium borohydride is then added portionwise. The reaction medium is stirred for 1 hour and then poured into 100 mL of water. After purification by chromatography on silica gel, the desired product is obtained in the form of a colourless oil (m=4 g; Y=100%).

Workup

  1. customAfter purification by chromatography on silica gel

Sources & evidence

ORD record
ord-9205c61af32d4e83aed778fc45781fe5
Source dataset
uspto-grants-2004_03
Patent number
US06706725B1

Reaction notes

Loading…