Methanol → 4,4,4-Trifluoro-1-(4-pyrazol-1-yl-phenyl)-butane-1,3-dione

HRID 1855361

Reaktionsgleichung

C[O-].[Na+].CO.[F:6][C:7]([F:14])([F:13])[C:8]([O:10]CC)=O.[N:15]1([C:20]2[CH:25]=[CH:24][C:23]([C:26](=[O:28])[CH3:27])=[CH:22][CH:21]=2)[CH:19]=[CH:18][CH:17]=[N:16]1>C(OC(C)(C)C)C>[F:14][C:7]([F:6])([F:13])[C:8](=[O:10])[CH2:27][C:26]([C:23]1[CH:22]=[CH:21][C:20]([N:15]2[CH:19]=[CH:18][CH:17]=[N:16]2)=[CH:25][CH:24]=1)=[O:28]

Komponenten

Reaktionsbedingungen

Temperatur: 20 °C

Versuchsvorschrift

A 5.4 N solution of sodium methoxide in methanol (3.0 mL, 16.2 mmol) was added drop wise over 10 min to a solution of ethyl trifluoro-acetate (1.81 mL, 15.2 mmol) in 2-ethoxy-2-methyl-propane (20 mL) at 20° C. followed by the addition of a suspension of 1-(4-pyrazol-1-yl-phenyl)-ethanone (2.57 g, 13.8 mmol) in 2-ethoxy-2-methyl-propane (10 mL). The reaction mixture was stirred for 22 h at 20° C. and then poured onto ice-water (50 mL). The mixture was extracted with ethyl acetate and the organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The remaining solid was recrystallized from ethyl acetate/heptane to give the title compound (2.47 g, 63%) as off-white solid. Mp 96° C.

Aufarbeitung

additionpoured onto ice-water (50 mL)
extractionThe mixture was extracted with ethyl acetate
washthe organic layer was washed with brine
dry with materialdried over sodium sulfate
customevaporated under reduced pressure
customThe remaining solid was recrystallized from ethyl acetate/heptane

Quellen und Nachweise

ORD-Eintrag: ord-35d4d44f7e334382a8d9b1f824d5df5c
Quelldatensatz: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08962834B2

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