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

HRID 1914255ノート

反応式

HRID 1914255 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-73a442c9383e4d0faba4b48e6ffc4030
出典データセット
uspto-grants-2013_12
特許番号
US08609897B2

反応ノート

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