(Dimethyl sulfide)trihydroboron → 4-(Trimethylsilyl)butan-1-ol

HRID 1735173Notes

Reaction equation

HRID 1735173 reaction equation
CSC.B.[CH3:5][Si:6]([CH3:14])([CH3:13])[CH2:7][CH2:8][CH2:9][C:10](O)=[O:11]>O1CCCC1>[CH3:5][Si:6]([CH3:14])([CH3:13])[CH2:7][CH2:8][CH2:9][CH2:10][OH:11]

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 128500874-Trimethylsilylbutanoic acid

Product 1

HCID 2628454-(Trimethylsilyl)butan-1-olYield 71.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.5 ml (11.4 mmol) of a 1 molar solution of borane dimethylsulfide was added to a cooled (0° C.) solution of 0.61 g (3.8 mmol) of 4-(trimethylsilyl)-butanoic acid in 20 ml of dry tetrahydrofuran. After work-up using the standard procedure (methanol, tetramethylethylene diamine) and flash chromatography purification on silica gel eluted with a 9:1 mixture of hexane and ethyl acetate, 0.4 g of 4-(trimethylsilyl)-1-butanol was obtained as a colorless liquid.

Workup

  1. customthe standard procedure (methanol, tetramethylethylene diamine) and flash chromatography purification on silica gel
  2. washeluted with a 9:1 mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-1131b47f6c294ab0b9f0272dd7b1acd6
Source dataset
uspto-grants-1996_07
Patent number
US05536732

Reaction notes

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