Sodium borohydride → HCID 11391116, compound

HRID 1468757Notes

Reaction equation

HRID 1468757 reaction equation
[Si:1]([O:8][CH2:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[Si:1]([O:8][CH2:9][CH:10]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[OH:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 135233382-(Tert-butyldimethylsilanyloxy)-1-phenylethanone

Product 1

HCID 11391116HCID 11391116, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(tert-butyldimethylsilanyloxy)-1-phenylethanone (2.5 g, 10 mmol, Example 4) in methanol (30 ml) added with sodium borohydride (378 mg, 10 mmol) at room temperature. The mixture was stirred at room temperature for 5.5 hours and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=3/1) to give 2-(tert-butyldimethylsilanyloxy)-1-phenylethanol (0.73 g, 2.9 mmol, 29%) as a colorless oil.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-72cbc16cebb24932838bfa7841923826
Source dataset
uspto-grants-2015_04
Patent number
US09006232B2

Reaction notes

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