تفاعل #1960506

معادلة التفاعل

6-ethoxy-3,4-difluoronaphthalen-2-ol

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

triphenylphosphine

DIAD

→

7-ethoxy-1,2-difluoro-3-[1-(4-propylcyclohexyl)prop-2-ynyloxy]naphthalene

المذيبات

water

THF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONare added over the course of 20 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 soln
5. 5
   أخرى, and the solution is dried
6. 6
   أخرىafter removal of the solvents
7. 7
   أخرىis purified by column chromatography (SiO2, n-heptane:MTBE=2:1)
8. 8
   أخرىThe further purification
9. 9
   أخرىis carried out by recrystallisation from n-heptane

الإجراء التجريبي

10.5 g (46.8 mmol) of 6-ethoxy-3,4-difluoronaphthalen-2-ol are initially introduced in 100 ml of THF together with 10.0 g (55.5 mmol) of 1-(4-propylcyclohexyl)prop-2-yn-1-ol and 15.0 g (57.2 mmol) of triphenylphosphine, and 11.5 ml (59.1 mmol) of DIAD are added over the course of 20 min with ice-cooling. After 18 h at RT, water 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 soln., and the solution is dried using sodium sulfate. The residue remaining after removal of the solvents is purified by column chromatography (SiO2, n-heptane:MTBE=2:1). The further purification is carried out by recrystallisation from n-heptane, giving 7-ethoxy-1,2-difluoro-3-[1-(4-propylcyclohexyl)prop-2-ynyloxy]naphthalene as a yellowish solid.

المصدر