تفاعل #1960487

معادلة التفاعل

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

المذيبات

THF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر