Hydrochloric Acid → 5,6-Difluoro-8-(4-propylcyclohexyl)-1,2,3,8-tetrahydropyrano[3,2-f]chromene

Participants

Reaction Steps

6.0 g (17.2 mmol) of 7,8-difluoro-6-[1-(4-propylcyclohexyl)prop-2-ynyloxy]-chroman are heated at 200° C. for 6 h together with 2.0 g (34.4 mmol) of potassium fluoride in 55 ml of N,N-diethylaniline. After cooling, water is added, and the mixture is acidified using 25% hydrochloric acid. The batch is extracted with MTBE, and the organic phase is washed with saturated sodium chloride solution. The solution is dried using sodium sulfate and evaporated to dryness. The crude product is purified by column chromatography (SiO2, 1-chlorobutane), giving 5,6-difluoro-8-(4-propylcyclohexyl)-1,2,3,8-tetrahydropyrano[3,2-f]chromene as a pale-brown oil.

Provenance & Evidence