Sodium Chloride → 1-(2-Methyl-4'-trifluoromethyl-biphenyl-4-yl)-heptan-1-ol

HRID 1669340Notes

Reaction equation

HRID 1669340 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8](=[O:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:5]=[CH:4][C:3]=1[C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1.[BH4-].[Na+].C(=O)(O)[O-].[Na+].[Cl-].[Na+]>C(O)C.C(OCC)(=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH:8]([OH:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:5]=[CH:4][C:3]=1[C:16]1[CH:17]=[CH:18][C:19]([C:22]([F:23])([F:24])[F:25])=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 597293991-(2-Methyl-4'-trifluoromethyl-biphenyl-4-yl)-heptan-1-one

Product 1

HCID 597294401-(2-Methyl-4'-trifluoromethyl-biphenyl-4-yl)-heptan-1-olYield 97%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 1-(2-methyl-4′-trifluoromethyl-biphenyl-4-yl)-heptan-1-one (0.516 g, 1.48 mmol) in ethanol (5 mL). Add sodium borohydride (0.224 g, 5.93 mmol) at 0° C. under inert atmosphere and stir three hours. Quench reaction with saturated solution of ammonium chloride, dilute with ethyl acetate. Wash organic phase with saturated sodium bicarbonate solution, then saturated sodium chloride solution. Dry organic fraction with Na2SO4, filter and concentrate under reduced pressure. Purify on silica gel chromatography (0-30% Ethyl acetate/hexanes gradient) to provide 0.5 g of title compound (97%).

Workup

  1. customQuench
  2. customreaction with saturated solution of ammonium chloride
  3. filtrationDry organic fraction with Na2SO4, filter
  4. concentrationconcentrate under reduced pressure
  5. customPurify on silica gel chromatography (0-30% Ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-371112f26bdc4d51ac5282419454333c
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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