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

HRID 748691ノート

反応式

HRID 748691 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

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 Example 5 was dissolved in toluene (20 ml). To the resulting solution were added 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 down and then, added with cyclohexanol (0.22 ml, 2.1 mmol) and cyanomethylenetri-n-butylphosphorane (500 mg, 2.08 mmol). The mixture was heated under reflux for 14 hours under an argon atmosphere. After the reaction mixture was allowed to cool down and concentrated under reduced pressure, the residue thus obtained was purified by silica gel chromatography (hexane:ethyl acetate=30:1) to yield a white solid. The resulting white solid was washed with hexane, whereby the title compound (188 mg, 62%) was obtained 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 down
  4. temperatureThe mixture was heated
  5. temperatureunder reflux for 14 hours under an argon atmosphere
  6. temperatureto cool down
  7. concentrationconcentrated under reduced pressure
  8. customthe residue thus obtained
  9. customwas purified by silica gel chromatography (hexane:ethyl acetate=30:1)
  10. customto yield a white solid
  11. washThe resulting white solid was washed with hexane, whereby the title compound (188 mg, 62%)
  12. customwas obtained as a white powder

出典と根拠

ORDレコード
ord-18b546c1cac44b4496c1bb01b2391806
出典データセット
uspto-grants-2008_07
特許番号
US07399775B2

反応ノート

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