Imidazole → 4-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloro-5-methoxyaniline

HRID 630385Notizen

Reaktionsgleichung

[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH2:9][OH:10])=[C:4]([O:11][CH3:12])[CH:3]=1.N1C=CN=[CH:14]1.Cl[Si:19]([CH:22]([CH3:24])[CH3:23])([CH3:21])[CH3:20]>CN(C)C=O>[Si:19]([O:10][CH2:9][C:5]1[C:4]([O:11][CH3:12])=[CH:3][C:2]([NH2:1])=[C:7]([Cl:8])[CH:6]=1)([C:22]([CH3:24])([CH3:14])[CH3:23])([CH3:21])[CH3:20]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of (4-amino-5-chloro-2-methoxyphenyl)methanol (intermediate 38; 1.5 g, 0.008 mol) in dimethylformamide (35 mL) was added imidazole (1.7 g, 0.02 mol). The mixture was cooled to 0° C. and chloro(isopropyl)dimethylsilane (2.5 g, 0.01 mol) was added dropwise. The reaction was stirred overnight at room temperature. The solvent was removed and the crude was partitioned between water and hexane, the organic layer was washed with water, sodium bicarbonate 4% and brine, dried, filtered and evaporated to dryness. The crude obtained was purified by column chromatography with silica gel, eluting with hexane/ethyl acetate (from 8/1 to 4/1). The title compound was obtained as a yellow solid (58%).

Aufarbeitung

customThe solvent was removed
customthe crude was partitioned between water and hexane
washthe organic layer was washed with water, sodium bicarbonate 4% and brine
customdried
filtrationfiltered
customevaporated to dryness
customThe crude obtained
customwas purified by column chromatography with silica gel
washeluting with hexane/ethyl acetate (from 8/1 to 4/1)

Quellen und Nachweise

ORD-Eintrag: ord-3059ad39c35c425c99e98cab15a03848
Quelldatensatz: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09315463B2

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