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

HRID 1607687ノート

反応式

HRID 1607687 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-87f4f2976bdf4a429ea6a3e28c5d5549
出典データセット
uspto-grants-1989_09
特許番号
US04866091

反応ノート

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