Tetrahydrofuran → 2-Tritylaminothiazole-4-methanol

참여 물질

반응 단계

A mixture comprising 2.6 g of ethyl 2-tritylaminothiazole-4-carboxylate and 10 ml of tetrahydrofuran was added dropwise under ice-cooling to a mixture comprising 0.24 g of lithium aluminum hydride and 30 ml of tetrahydrofuran, under a stream of nitrogen. After completion of the dropwise addition, the resulting mixture was stirred at room temperature for 3 hours, and then with heating under reflux for one hour. Ethyl acetate and then water were added to the reaction mixture under ice-cooling, the organic layer was separated off, and the aqueous layer was re-extracted with ethyl acetate. The combined ethyl acetate extract was washed with saturated aqueous sodium chloride solution, and then dried over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography, using as eluent a 1:1 by volume mixture of benzene and ethyl acetate. The product was recrystallized from a mixture of ethyl acetate, acetone and n-hexane. giving the desired compound as a pale yellow powder.

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