Sodium borohydride → 4-[5-Fluoro-2-(trifluoromethyl)phenyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}cyclohexanol

HRID 1914255Notes

Reaction equation

HRID 1914255 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:28]([F:31])([F:30])[F:29])=[C:6]([C:8]2([S:15]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]2)[CH:7]=1.[BH4-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:28]([F:31])([F:29])[F:30])=[C:6]([C:8]2([S:15]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:25])([F:26])[F:27])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH2:9][CH2:10][CH:11]([OH:14])[CH2:12][CH2:13]2)[CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 584850624-[5-Fluoro-2-(trifluoromethyl)phenyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}cyclohexanone

Product 1

HCID 584850604-[5-Fluoro-2-(trifluoromethyl)phenyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}cyclohexanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 1 L 3-neck round bottom flask equipped with a nitrogen bubbler, thermocouple, stir bar and condenser was charged with 4-[5-fluoro-2-(trifluoromethyl)phenyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}cyclohexanone (45 g, 96 mmol) in ethanol (464 ml). Next sodium borohydride (9.67 g, 256 mmol) was added and the reaction was stirred for 30 min. The reaction was quenched by adding HCl (200 ml, 2N) slowly over 10 minutes and then the reaction was poured into HCl (2 L, 2N) and extracted with ethyl acetate (3×1 L). The organic layers were washed with brine, dried over MgSO4, filtered and concentrated to provide 4-[5-fluoro-2-(trifluoromethyl)phenyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}cyclohexanol.

Workup

  1. customA 1 L 3-neck round bottom flask equipped with a nitrogen bubbler
  2. stirringthe reaction was stirred for 30 min
  3. customThe reaction was quenched
  4. additionby adding HCl (200 ml, 2N) slowly over 10 minutes
  5. additionthe reaction was poured into HCl (2 L, 2N)
  6. extractionextracted with ethyl acetate (3×1 L)
  7. washThe organic layers were washed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-73a442c9383e4d0faba4b48e6ffc4030
Source dataset
uspto-grants-2013_12
Patent number
US08609897B2

Reaction notes

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