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

HRID 1090327Notes

Reaction equation

HRID 1090327 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

To a solution of 3.58 g (15.4 mmol) of methyl (-)-3-t-butyldimethylsilyloxybutyrate dissolved in 30 ml of methanol, 30 ml of 1N potassium hydroxide was added and the mixture was stirred for 15 hours. After almost all methanol was distilled away, the resultant was acidified with 1N hydrochloric acid and extracted with diethyl ether. The extract was washed with a saturated solution of NaCl, dried with anhydrous magnesium sulfate and concentrated under reduced pressure to give 3.18 g of (-)-3-t-butyldimethylsilyloxybutyric acid (yield: 95%).

Workup

  1. distillationAfter almost all methanol was distilled away
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with a saturated solution of NaCl
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bcb5c6e0d3654d4cb57ce5f4e68ec316
Source dataset
uspto-grants-1992_01
Patent number
US05081238

Reaction notes

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