Sodium hydride → HCID 20624493, compound

Participants

Reaction Steps

2-(Benzo[3,4-d]1,3-dioxolan-5-yl)-4-hydroxymethyl-1,3-thiazole prepared in Example 20(200 mg, 0.85 mmol) was dissolved in N,N-dimethylformamide(5 ml), and sodium hydride(30.7 mg, 1.28 mmol) was added thereto at 0-5° C. To this mixture was added dropwise 2-(methane sulfonyloxymethyl)pyridine(315 mg) dissolved in 1 ml of tetrahydrofuran, and the resulting mixture was stirred for 2 hours at room temperature. Saturated sodium bicarbonate solution was added to the reaction mixture, which was then extracted with a solvent mixture of ethyl acetate/n-hexane(1/1, v/v). The extract was washed with saturated saline solution, dried over anhydrous sodium sulfate, and concentrated. The concentrate was subjected to silica gel column chromatography(eluent: ethyl acetate/n-hexane=1/2, v/v) to give the title compound(180 mg, Yield 65%) as an ivory solid.

Provenance & Evidence