Imidazole → 6-(3-tert-butyldimethylsilyloxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran

HRID 1420761

Reaktionsgleichung

[OH:1][C:2]1[CH:3]=[C:4]([S:8][C:9]2[CH:21]=[CH:20][C:12]3[O:13][C:14]([CH3:19])([CH3:18])[C:15]([CH3:17])=[CH:16][C:11]=3[CH:10]=2)[CH:5]=[CH:6][CH:7]=1.N1C=CN=C1.[Si:27](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28].O>CN(C)C=O>[Si:27]([O:1][C:2]1[CH:3]=[C:4]([S:8][C:9]2[CH:21]=[CH:20][C:12]3[O:13][C:14]([CH3:18])([CH3:19])[C:15]([CH3:17])=[CH:16][C:11]=3[CH:10]=2)[CH:5]=[CH:6][CH:7]=1)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

6-(3-Hydroxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran (2.2 g) (see Preparation 9) was dissolved in dry dimethylformamide (4 ml) and imidazole (1.1 g) and tert-butyidimethylsilyl chloride (1.2 g) were added. The flask was fitted with a calcium chloride drying tube and the mixture was stirred at 40° C. for one hour. Water was added and the mixture was extracted with diethyl ether. The organic extract was washed with aqueous sodium hydrogen carbonate solution (×2), dried (anhydrous sodium sulphate), the solvent removed under reduced pressure and the crude product chromatographed on silica using (4:1 hexane:dichloromethane as the eluent to yield 6-(3-tert-Butyldimethylsilyloxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran (2.84 g) as an oil.

Aufarbeitung

customThe flask was fitted with a calcium chloride drying tube
extractionthe mixture was extracted with diethyl ether
extractionThe organic extract
washwas washed with aqueous sodium hydrogen carbonate solution (×2)
dry with materialdried (anhydrous sodium sulphate)
customthe solvent removed under reduced pressure
customthe crude product chromatographed on silica using (4:1 hexane

Quellen und Nachweise

ORD-Eintrag: ord-2d4071625aac47939e96ece4a00f95dc
Quelldatensatz: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06071938

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