Sodium borohydride → HCID 178455058, compound

HRID 1007964Notes

Reaction equation

HRID 1007964 reaction equation
[BH4-].[Na+].[Si:3]([O:10][C:11]1[CH:16]=[C:15]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH:14]=[CH:13][C:12]=1[CH:25]1[CH2:30][CH2:29][C:28](=[O:31])[CH2:27][CH2:26]1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]>C(O)C>[Si:3]([O:10][C:11]1[CH:16]=[C:15]([O:17][Si:18]([C:21]([CH3:22])([CH3:23])[CH3:24])([CH3:20])[CH3:19])[CH:14]=[CH:13][C:12]=1[C@@H:25]1[CH2:26][CH2:27][C@H:28]([OH:31])[CH2:29][CH2:30]1)([C:6]([CH3:7])([CH3:8])[CH3:9])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 223378144-(2,4-Bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexan-1-one

Product 1

HCID 178455058HCID 178455058, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (164 mg) was added to a stirred solution of 4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexanone (1.57 g) in ethanol (50 ml) at 0° C. After 18 hr at room temperature, the mixture was partitioned between 2M HCl (20 ml), water (40 ml) and ethyl acetate (50 ml) and the aqueous layer was re-extracted with ethyl acetate (2×50 ml). The combined organic extracts were washed with brine (40 ml), dried over magnesium sulfate and evaporated in vacuo. The residue was purified using flash column chromatography (SiO2, ethyl acetate/petrol, 3:17 v/v) to give the trans-title compound as a white solid (546 mg, 35%), and the cis-title compound as a white solid (83 mg, 5%).

Workup

  1. customthe mixture was partitioned between 2M HCl (20 ml), water (40 ml) and ethyl acetate (50 ml)
  2. extractionthe aqueous layer was re-extracted with ethyl acetate (2×50 ml)
  3. washThe combined organic extracts were washed with brine (40 ml)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified

Sources & evidence

ORD record
ord-05fa14dcfefc496f95c602cef796348c
Source dataset
uspto-grants-2004_09
Patent number
US06797731B2

Reaction notes

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