Reaction #1960487

Reaction equation

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

Solvents

THF

Conditions

Workup

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

Procedure

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.

Source