Sodium borohydride → HCID 178455060, compound

HRID 585675Notes

Reaction equation

HRID 585675 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].[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 178455060HCID 178455060, 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 2 hr at 0° C. and then 18 hr at room temperature, the reaction 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 compounds as a white solid (83 mg, 5%).

Workup

  1. custom18 hr at room temperature, the reaction 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-b59a4b6d91d844648ebe40da4c39126f
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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