反応 #1960487

反応方程式

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

溶媒

THF

反応条件

後処理

1. 1
   workup.ADDITIONare added over the course of 30 min with ice-
2. 2
   温度cooling
3. 3
   抽出the mixture is extracted a number of times with MTBE
4. 4
   洗浄The combined organic phases are washed with water and saturated sodium chloride solution
5. 5
   その他the solution is dried
6. 6
   その他after removal of the solvents
7. 7
   その他is purified by column chromatography (SiO2, n-pentane:MTBE=2:1)

実験手順

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.

出典