Реакция #1960487

Уравнение реакции

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

Растворители

THF

Условия реакции

Обработка

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

Методика

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.

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