3,4-dihydro-2H-pyran → 6-[2-(2-Ethyloxiran-2-yl)ethyl]-3,4-dihydro-2H-pyran

Participants

Reaction Steps

To a stirred solution of 3.2 g of dihydropyran and 1.4 g of dry tetrahydrofuran at 0° C. was added dropwise 50 ml 2 M tert-butyl lithium. The reaction was allowed to warm to room temperature, then cooled to -10° to -20° C., and 10 g of 1,2-epoxy-2-(ethyl)-4-iodobutane and 0.7 g of hexamethylphosphoramide was added dropwise over 10 minutes. After stirring for 2 hours at -15° to -20° C., 6-8 ml of dry tetrahydrofuran was added. The reaction mixture was allowed to warm to room temperature, stirred for a total of 2 hours, 40-50 ml of hexane was added, and the mixture was washed with water and then with a saturated sodium chloride and sodium bisulfite mixture, dried and vacuum stripped to give 6 g of the desired material as an oil.

Provenance & Evidence