Sodium borohydride → 1-[4'-(Trifluoromethyl)-4-biphenylyl]-1-pentanol

HRID 1391746Notes

Reaction equation

HRID 1391746 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:20])[CH2:16][CH2:17][CH2:18][CH3:19])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[BH4-].[Na+]>C1COCC1.O>[F:1][C:2]([F:21])([F:22])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]([OH:20])[CH2:16][CH2:17][CH2:18][CH3:19])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 586298951-[4'-(Trifluoromethyl)-4-biphenylyl]-1-pentanone

Product 1

HCID 596742571-[4'-(Trifluoromethyl)-4-biphenylyl]-1-pentanolYield 97.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[4′-(trifluoromethyl)-4-biphenylyl]-1-pentanone (500 mg, 1.63 mmol) in THF (16 mL) and water (8 mL) under nitrogen at 0° C. (ice/water bath) was added sodium borohydride (74 mg, 1.96 mmol) portion-wise. After stirring the mixture for 1 hour at rt, the reaction was diluted with water (30 mL) and extracted into EtOAc (3×30 mL). The combined organic extract was separated, dried (MgSO4) and reduced under vacuum to afford the title compound as a colourless gum (490 mg).

Workup

  1. extractionextracted into EtOAc (3×30 mL)
  2. extractionThe combined organic extract
  3. customwas separated
  4. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-30391b4cdd614f13af4d402ffffa0cad
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

Loading…