2-Butyn-1-ol → 5-(2-Methylcyclohexyl)-3-(2-butynyloxy)-1,2,4-thiadiazole

Participants

Reaction Steps

160 mg of 3-methylsulfonyl-5-(2-methylcyclohexyl)-1,2,4-thiadiazole and 52 mg of 2-butyn-1-ol were dissolved in 1.5 ml of N,N-dimethylformamide, 32 mg of sodium hydride (60% in oil) was added thereto under ice-cooling, and the reaction mixture was stirred for 1 hour under ice-cooling and for 12 hours at room temperature. Then, the reaction mixture was added to saturated brine, and extracted with t-butyl methyl ether. The organic layer was concentrated under reduced pressure, and the residue obtained was subjected to silica gel column chromatography to give 39 mg of 5-(2-methylcyclohexyl)-3-(2-butynyloxy)-1,2,4-thiadiazole (hereinafter referred to as the present invention compound (10)).

Provenance & Evidence