1,4-Butanediol monovinyl ether → 2-[1-[(4-Chlorophenyl)sulfonyl]-5-vinyloxypentyl]-1,4-difluorobenzene

HRID 748683

반응식

HRID 748683 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]([O:22][CH2:23][CH2:24][CH2:25][CH2:26]O)=[CH2:21].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]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])[CH2:26][CH2:25][CH2:24][CH2:23][O:22][CH:20]=[CH2:21])(=[O:10])=[O:9])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 873291,4-Butanediol monovinyl etherHCID 4622928CyanomethylenetributylphosphoraneHCID 99010282-(((4-Chlorophenyl)sulfonyl)methyl)-1,4-difluorobenzene

생성물 1

HCID 597507152-[1-[(4-Chlorophenyl)sulfonyl]-5-vinyloxypentyl]-1,4-difluorobenzene

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

The 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (0.94 g, 3.1 mmol) obtained in Example 5 was dissolved in toluene (30 ml). After addition of 4-vinyloxy-1-butanol (0.51 ml, 4.2 mmol) and cyanomethylenetri-n-butylphosphorane (1.0 g, 4.1 mmol), the resulting mixture was heated under reflux for 3 days under an argon atmosphere. The reaction mixture was allowed to cool down and then concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (hexane:ethyl acetate=10:1) to yield a white solid. The resulting white solid was washed with hexane, whereby the title compound (0.97 g, 78%) was obtained as a white powder.

후처리

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 3 days under an argon atmosphere
  3. temperatureto cool down
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by silica gel chromatography (hexane:ethyl acetate=10:1)
  7. customto yield a white solid
  8. washThe resulting white solid was washed with hexane, whereby the title compound (0.97 g, 78%)
  9. customwas obtained as a white powder

출처 및 근거

ORD 기록
ord-f027a99fc0fb4a52b78d728e0625c33e
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07399775B2

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