Methanol → (4'-{[Tert-butyl(dimethyl)silyl]oxy}-3'-chloro-2',6'-dimethylbiphenyl-3-yl)methanol

HRID 15655Notes

Reaction equation

HRID 15655 reaction equation
[Si:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]=[O:23])[CH:17]=2)=[C:11]([CH3:24])[C:10]=1[Cl:25])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CO.[BH4-].[Na+].O>O1CCCC1>[Si:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][OH:23])[CH:17]=2)=[C:11]([CH3:24])[C:10]=1[Cl:25])([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 59342609HCID 59342609, compound

Product 1

HCID 59342577(4'-{[Tert-butyl(dimethyl)silyl]oxy}-3'-chloro-2',6'-dimethylbiphenyl-3-yl)methanolYield 97.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4′-{[tert-butyl(dimethyl)silyl]oxy}-3′-chloro-2′,6′-dimethylbiphenyl-3-carbaldehyde (1.78 g, 4.75 mmol) in a mixed solvent of in tetrahydrofuran (10 mL) and methanol (5 mL) was added sodium borohydride (90%, 90 mg, 2.38 mmol) under ice-cooling, and the mixture was stirred at the same temperature for 2 hr under nitrogen atmosphere. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-40:60) to give the title compound (1.74 g, yield 97%) as a colorless oil.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-40:60)

Sources & evidence

ORD record
ord-41143ddd9d4847378a0291bfb01b6e12
Source dataset
uspto-grants-2010_06
Patent number
US07732626B2

Reaction notes

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