Reacción #1960494

Ecuación de reacción

hydrochloric acid

7,8-difluoro-2-pentyl-6-[1-(4-propylcyclohexyl)prop-2-ynyloxy]chroman

potassium fluoride

water

→

5,6-difluoro-3-pentyl-8-(4-propylcyclohexyl)-1,2,3,8-tetrahydropyrano[3,2-f]chromene

Disolventes

N,N-diethylaniline

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling
2. 2
   ExtracciónThe batch is extracted with MTBE
3. 3
   Lavadothe organic phase is washed with saturated sodium chloride solution
4. 4
   OtroThe solution is dried
5. 5
   Otroevaporated to dryness
6. 6
   OtroThe crude product is purified by column chromatography (SiO2, 1-chlorobutane:pentane=4:1)

Procedimiento

9.7 g (23.2 mmol) of 7,8-difluoro-2-pentyl-6-[1-(4-propylcyclohexyl)prop-2-ynyloxy]chroman are heated at 200° C. for 6 h together with 2.7 g (46.5 mmol) of potassium fluoride in 75 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:pentane=4:1), giving 5,6-difluoro-3-pentyl-8-(4-propylcyclohexyl)-1,2,3,8-tetrahydropyrano[3,2-f]chromene as a pale-brown oil.

Fuente