Sodium borohydride → 4-Methyl-1-(4-(trifluoromethyl)phenyl)pentan-1-ol

HRID 220738

Reaction equation

HRID 220738 reaction equation
[BH4-].[Na+].[CH3:3][CH:4]([CH3:19])[CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)=[O:8]>CCO>[CH3:3][CH:4]([CH3:19])[CH2:5][CH2:6][CH:7]([C:9]1[CH:10]=[CH:11][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:13][CH:14]=1)[OH:8]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 469413964-Methyl-1-(4-(trifluoromethyl)phenyl)pentan-1-one2×

Product 1

HCID 468563994-Methyl-1-(4-(trifluoromethyl)phenyl)pentan-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (2.8 g, 0.074 mol) was added portionwise to a solution of 4-methyl-1-[4-(trifluoromethyl)phenyl]pentan-1-one [Intermediate 1; Step 1] in EtOH (50 mL) cooled in ice. When addition was complete (30 min) the mixture was stirred at RT for 1 h then quenched with NH4Cl solution (50 mL) followed by 2N HCl (20 mL). Extraction with ether (3×50 mL) followed by drying (MgSO4) and concentration of the organic phase gave 4-methyl-1-(4-(trifluoromethyl)phenyl)pentan-1-ol as a colourless oil.

Workup

  1. temperaturecooled in ice
  2. additionWhen addition
  3. custom(30 min)
  4. customthen quenched with NH4Cl solution (50 mL)
  5. extractionExtraction with ether (3×50 mL)
  6. dry with materialby drying (MgSO4) and concentration of the organic phase

Sources & evidence

ORD record
ord-6ae252e3dcf8477faafa09aaac013c5b
Source dataset
uspto-grants-2012_06
Patent number
US08203004B2

Linked notes

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