Water → 2-(4-(2,2-Diethoxyethoxy)-2,3-difluorophenyl)ethanol

HRID 471168

Reaktionsgleichung

C(=O)([O-])[O-].[Cs+].[Cs+].[F:7][C:8]1[C:13]([F:14])=[C:12]([CH2:15][CH2:16][OH:17])[CH:11]=[CH:10][C:9]=1[OH:18].Br[CH2:20][CH:21]([O:25][CH2:26][CH3:27])[O:22][CH2:23][CH3:24].O>CN(C=O)C>[CH2:23]([O:22][CH:21]([O:25][CH2:26][CH3:27])[CH2:20][O:18][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][OH:17])=[C:13]([F:14])[C:8]=1[F:7])[CH3:24]

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

Cesium carbonate (0.99 g) was added to a solution of 2,3-difluoro-4-(2-hydroxyethyl)phenol (example 77, step b) (0.44 g) and 2-bromo-1,1-diethoxyethane (0.4 mL) in DMF (10 mL). The resulting suspension was heated at 90° C. for 18 h. The reaction was allowed to cool and poured into water (100 mL). The aqueous mixture was extracted with diethylether (3×100 mL). The combined organic solutions were washed with water (200 mL) and brine (200 mL), dried over magnesium sulfate, filtered and evaporated. The crude material was purified by silica gel chromatography eluting with isohexane to 1:1 ethyl acetate:isohexane gradient. The fractions containing product were combined and evaporated to give the subtitled compound as a yellow oil. Yield 0.49 g.

Aufarbeitung

temperatureto cool
extractionThe aqueous mixture was extracted with diethylether (3×100 mL)
washThe combined organic solutions were washed with water (200 mL) and brine (200 mL)
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated
customThe crude material was purified by silica gel chromatography
washeluting with isohexane to 1:1 ethyl acetate
additionThe fractions containing product
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-3468fecfd6244ff185c169c4e1177245
Quelldatensatz: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08629271B2

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