Potassium Hydroxide → (-)-3-t-Butyldimethylsilyloxybutyric acid

HRID 247700Notes

Reaction equation

HRID 247700 reaction equation
[Si:1]([O:8][CH:9]([CH3:15])[CH2:10][C:11]([O:13]C)=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH-].[K+]>CO>[Si:1]([O:8][CH:9]([CH3:15])[CH2:10][C:11]([OH:13])=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 137127793-(tert-Butyldimethylsiloxy)butyric acid methyl ester

Product 1

HCID 13712781(-)-3-t-Butyldimethylsilyloxybutyric acidYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

There was dissolved 3.58 g (15.4 mmol) of methyl (-)-3-t-butyldimethylsilyloxybutyrate in 30 ml of methanol, to which 30 ml of 1 N potassium hydroxide was added and the mixture was stirred for 15 minutes. After distilling away most methanol from the mixture, the solution was acidified with 1 N hydrochloric acid and extracted with diethyl ether. The extract was washed with a saturated aqueous solution of sodium chloride and dried with anhydrous magnesium sulfate, which was concentrated under reduced pressue to give 3.18 g of (-)-3-t-butyldimethylsilyloxybutyric acid.

Workup

  1. distillationAfter distilling away most methanol from the mixture
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried with anhydrous magnesium sulfate, which
  5. concentrationwas concentrated under reduced pressue

Sources & evidence

ORD record
ord-6421b2b7858243bcb4b07856fe341588
Source dataset
uspto-grants-1987_11
Patent number
US04709064

Reaction notes

Loading…