Ethyl Acetate → 2'-(2,4-Difluorophenoxy)-4'-(3-oxo-1-butenyl)methanesulfonanilide

HRID 1607687

반응식

HRID 1607687 반응식
[F:1][C:2]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[CH:15]=[C:14]([CH:16]=O)[CH:13]=[CH:12][C:6]=1[NH:7][S:8]([CH3:11])(=[O:10])=[O:9].C1(P(=[CH:42][C:43](=[O:45])[CH3:44])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C>CS(C)=O>[F:1][C:2]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[CH:15]=[C:14]([CH:16]=[CH:42][C:43](=[O:45])[CH3:44])[CH:13]=[CH:12][C:6]=1[NH:7][S:8]([CH3:11])(=[O:10])=[O:9]

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 150381-(Triphenylphosphoranylidene)acetoneHCID 104041542'-(2,4-Difluorophenoxy)-4'-formylmethanesulfonanilide

생성물 1

HCID 539161362'-(2,4-Difluorophenoxy)-4'-(3-oxo-1-butenyl)methanesulfonanilide수율 38.7%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
80 °C

실험 절차

A mixture of 2'-(2,4-difluorophenoxy)-4'-formylmethanesulfonanilide (2.3 g) and triphenylphosphoranylideneacetone (2.3 g) in dimethylsulfoxide (10 ml) was stirred for 13 hours at 80° C. After cooling of the mixture, ethyl acetate was added, and the resulting mixture was washed with water, then dried. The ethyl acetate layer was evaporated to dryness and the residue was purified by column chromatography on silica gel (80 g) eluting with a mixture of chloroform and methanol (200:1) and further recrystallized from ethanol to give pale yellow needles of 2'-(2,4-difluorophenoxy)-4'-(3-oxo-1-butenyl)methanesulfonanilide (1.0 g).

후처리

  1. additionwas added
  2. washthe resulting mixture was washed with water
  3. customdried
  4. customThe ethyl acetate layer was evaporated to dryness
  5. customthe residue was purified by column chromatography on silica gel (80 g)
  6. washeluting with a mixture of chloroform and methanol (200:1)
  7. customfurther recrystallized from ethanol

출처 및 근거

ORD 기록
ord-87f4f2976bdf4a429ea6a3e28c5d5549
출처 데이터셋
uspto-grants-1989_09
특허 번호
US04866091

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