Imidazole → (2Z)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-en-1-ol

HRID 1437596

Reaktionsgleichung

[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](/[C:11](=[C:14](\[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)/[CH2:15][OH:16])/[CH2:12][OH:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3].N1C=CN=C1.[CH3:28][C:29]([Si:32](Cl)([CH3:34])[CH3:33])([CH3:31])[CH3:30]>C1COCC1.ClCCl.[Cl-].[Na+].O>[Si:32]([O:16][CH2:15]/[C:14](/[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[C:11](/[C:8]1[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=1)\[CH2:12][OH:13])([C:29]([CH3:31])([CH3:30])[CH3:28])([CH3:34])[CH3:33]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

To a solution of 110 g of (2Z)-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-ene-1,4-diol and 50 g of imidazole in 1 L of THF stirred at −78° C., a solution 51 g of TBSCl in 250 mL of dichloromethane was added dropwise. The resulting mixture was stirred at −78° C. for 30 min. Brine was then added and warmed to room temperature. The organic phase was separated and the aqueous phase was extracted with EtOAc. The organic phases were combined and dried over Na2SO4 and evaporated. The resulting crude material was purified by flash chromatography to afford 25.6 g of the title compound as a white solid. 1H NMR (acetone-d6, 500 MHz): a 7.69 (d, 2H), 7.37 (d, 2H), 7.18-7.04 (m, 5M), 4.77 (s, 2H), 4.65 (d, 2H), 3.96 (t, 1H, OH), 3.03 (s, 3H), 0.84 (s, 9H), 0.01 (s, 6H).

Aufarbeitung

temperaturewarmed to room temperature
customThe organic phase was separated
extractionthe aqueous phase was extracted with EtOAc
dry with materialdried over Na2SO4
customevaporated
customThe resulting crude material was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag: ord-e9024b6858804734804e714fdf90e9db
Quelldatensatz: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07622502B2

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