Cyclohexanol → 2-[[(4-Chlorophenyl)sulfonyl](cyclohexyl)methyl]-1,4-difluorobenzene

HRID 2080374ノート

反応式

HRID 2080374 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH:20]1(O)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C(C=P(CCCC)(CCCC)CCCC)#N>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 7966Cyclohexanol2 回HCID 4622928Cyanomethylenetributylphosphorane2 回HCID 99010282-(((4-Chlorophenyl)sulfonyl)methyl)-1,4-difluorobenzene

生成物 1

HCID 112576272-[[(4-Chlorophenyl)sulfonyl](cyclohexyl)methyl]-1,4-difluorobenzene収率 62%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

The 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (240 mg, 0.793 mmol) obtained in Referential Example 1 was dissolved in toluene (20 ml). After addition of cyclohexanol (0.11 ml, 1.0 mmol) and cyanomethylenetri-n-butylphosphorane (250 mg, 1.0 mmol), the resulting mixture was heated under reflux for 14 hours under an argon atmosphere. The reaction mixture was allowed to cool and then, cyclohexanol (0.22 ml, 2.1 mmol) and cyanomethylenetri-n-butylphosphorane (500 mg, 2.08 mmol) were added thereto. Under an argon atmosphere, the resulting mixture was heated under reflux for 14 hours. The reaction mixture was allowed to cool and concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (hexane:ethyl acetate=30:1) to give a white solid. The white solid was washed with hexane to give the title compound (188 mg, 62%) as a white powder.

後処理

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 14 hours under an argon atmosphere
  3. temperatureto cool
  4. temperatureUnder an argon atmosphere, the resulting mixture was heated
  5. temperatureunder reflux for 14 hours
  6. temperatureto cool
  7. concentrationconcentrated under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by silica gel chromatography (hexane:ethyl acetate=30:1)
  10. customto give a white solid
  11. washThe white solid was washed with hexane

出典と根拠

ORDレコード
ord-1c2cf0daba3b4341916c2614462c2764
出典データセット
uspto-grants-2011_04
特許番号
US07932271B2

反応ノート

読み込み中…