Ethanol → HCID 70648001, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5.949 g of 4-methyithiazole in 5 mL of tetrahydrofuran was added dropwise to 38 mL of a 1.6-M n-butyllithium/n-hexane solution in 6 mL of tetrahydrofuran under cooling at −60° C. After the mixture was stirred for 1.5 hours, a solution of 8.434 g of 4-chlorobenzaldehyde in 20 mL of tetrahydrofuran was added dropwise thereto. After the mixture was stirred at the same temperature for 1.8 hours, it took 2 hours to bring back to a room temperature, and then 15 mL of 50% ethanol aqueous solution was added to the mixture. The reaction solution was poured into water, and diethyl ether was added thereto, and the resulting mixture was subjected to extraction. The extract was washed with a saturated saline solution and then dried over magnesium sulfate. The solvent was distilled off, and then the raw product was purified by silica gel column chromatography (hexane/ethyl acetate (volume ratio)=2:1 to 1:1) to give the title compound (10.602 g (74%)).

Provenance & Evidence