Sodium borohydride → 1-(4'-Trifluoromethyl-biphenyl-4-yl)-butan-2-ol

HRID 1669289Notes

Reaction equation

HRID 1669289 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16](=[O:19])[CH2:17][CH3:18])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[BH4-].[Na+]>C(O)C>[F:1][C:2]([F:20])([F:21])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([OH:19])[CH2:17][CH3:18])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 673416551-(4'-Trifluoromethyl-biphenyl-4-yl)-butan-2-one

Product 1

HCID 673421621-(4'-Trifluoromethyl-biphenyl-4-yl)-butan-2-olYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To an ethanol (2 mL) solution of 1-(4′-trifluoromethyl-biphenyl-4-yl)-butan-2-one (0.093 g, 0.32 mmol) is added sodium borohydride (0.048 g, 1.27 mmol) at 0° C. The reaction mixture is stirred one hour at 0° C., quenched by saturated sodium bicarbonate solution (1 mL) and stirred for five minutes, extracted with ethyl acetate. Organic phase is washed with saturated sodium bicarbonate and brine dried over sodium sulfate, filtered and concentrated to give 0.088 g (0.30 mmol, 94%) of title compound.

Workup

  1. customquenched by saturated sodium bicarbonate solution (1 mL)
  2. stirringstirred for five minutes
  3. extractionextracted with ethyl acetate
  4. washOrganic phase is washed with saturated sodium bicarbonate and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ba3e0d99e1374258a89fd36e1f9329ea
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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