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

HRID 1607687

Reaktionsgleichung

[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]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-87f4f2976bdf4a429ea6a3e28c5d5549
Quelldatensatz: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04866091

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