Sodium borohydride → 2(S)-t-Butyldimethylsilyloxy-2-phenylethanol

HRID 1901198Notes

Reaction equation

HRID 1901198 reaction equation
[BH4-].[Na+].[Si:3]([O:10][C@@H:11]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:12](OCC)=[O:13])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]>CO>[Si:3]([O:10][C@@H:11]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH2:12][OH:13])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 10968419ethyl (S)-alpha-(t-butyldimethylsilyloxy)-alpha-phenylacetate

Product 1

HCID 228670812(S)-t-Butyldimethylsilyloxy-2-phenylethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

15.5 g of sodium borohydride were added in portions, whilst ice-cooling, to a solution of 20 g of ethyl (S)-α-t-butyldimethylsilyloxy-α-phenylacetate [prepared as described in step (a) above] in 500 ml of absolute methanol, and the resulting mixture was stirred overnight at room temperature. At the end of this time, 10 g of sodium borohydride were added in portions, whilst ice-cooling. The reaction mixture was then stirred at room temperature for 5 hours, after which it was concentrated by evaporation under reduced pressure, and the concentrate was mixed with water and ethyl acetate. The ethyl acetate layer was separated, washed with water and dried over anhydrous sodium sulfate, and then the solvent was removed by distillation under reduced pressure, to give the title compound as a crude product.

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was then stirred at room temperature for 5 hours
  3. concentrationafter which it was concentrated by evaporation under reduced pressure
  4. additionthe concentrate was mixed with water and ethyl acetate
  5. customThe ethyl acetate layer was separated
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-240dca1db7e84c01aadd378b11569c36
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

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