Acetone → (4'-((Tert-butyldimethylsilyl)oxy)-2',6'-dimethylbiphenyl-3-yl)methanol

HRID 2280635Notes

Reaction equation

HRID 2280635 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])[CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+].CC(C)=O>CO>[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])[CH:10]=1)([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 598383304'-{[Tert-butyl(dimethyl)silyl]oxy}-2',6'-dimethylbiphenyl-3-carbaldehyde

Product 1

HCID 59838328(4'-((Tert-butyldimethylsilyl)oxy)-2',6'-dimethylbiphenyl-3-yl)methanolYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4′-((tert-Butyldimethylsilyl)oxy)-2′,6′-dimethylbiphenyl-3-carbaldehyde 3e (2.60 g, 38.10 mmol) was dissolved in 80 mL of methanol, followed by addition of sodium borohydride (1.66 g, 43.95 mmol). The reaction mixture was stirred for 3 hours. The resulting mixture was mixed with 50 mL of acetone and concentrated under reduced pressure. The residue was mixed with 200 mL of ethyl acetate, washed with water (60 mL×2), dried with anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the crude title compound (4′-((tert-butyldimethylsilyl)oxy)-2′,6′-dimethylbiphenyl-3-yl)methanol 3f (9.80 g, yield 98.0%) as a colorless oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was mixed with 200 mL of ethyl acetate
  3. washwashed with water (60 mL×2)
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f7d0f6a2356547a0b83951d1c3f1ba6e
Source dataset
uspto-grants-2015_09
Patent number
US09139548B2

Reaction notes

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