Reacción #1960487

Ecuación de reacción

7,8-difluorochroman-6-ol

1-(4-propylcyclohexyl)-prop-2-yn-1-ol

triphenylphosphine

DIAD

sodium chloride

→

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

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONare added over the course of 30 min with ice-
2. 2
   Temperaturacooling
3. 3
   Extracciónthe mixture is extracted a number of times with MTBE
4. 4
   LavadoThe combined organic phases are washed with water and saturated sodium chloride solution
5. 5
   Otrothe solution is dried
6. 6
   Otroafter removal of the solvents
7. 7
   Otrois purified by column chromatography (SiO2, n-pentane:MTBE=2:1)

Procedimiento

5.0 g (26.9 mmol) of 7,8-difluorochroman-6-ol are initially introduced in 65 ml of THF together with 5.33 g (29.6 mmol) of 1-(4-propylcyclohexyl)-prop-2-yn-1-ol and 8.45 g (32.2 mmol) of triphenylphosphine, and 6.79 ml (34.9 mmol) of DIAD are added over the course of 30 min with ice-cooling. After 19 h at RT, semi-saturated sodium chloride solution is added, and the mixture is extracted a number of times with MTBE. The combined organic phases are washed with water and saturated sodium chloride solution, and the solution is dried using sodium sulfate. The residue remaining after removal of the solvents is purified by column chromatography (SiO2, n-pentane:MTBE=2:1), giving 7,8-difluoro-6-[1-(4-propylcyclohexyl)prop-2-ynyloxy]chroman as a pale-brown oil.

Fuente