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

HRID 2080374노트

반응식

HRID 2080374 반응식
[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

참가 물질

5

반응물 3

HCID 7966Cyclohexanol2회HCID 4622928Cyanomethylenetributylphosphorane2회HCID 99010282-(((4-Chlorophenyl)sulfonyl)methyl)-1,4-difluorobenzene

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1c2cf0daba3b4341916c2614462c2764
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932271B2

반응 노트

불러오는 중…