Реакция #1960506

Уравнение реакции

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

Растворители

water

THF

Условия реакции

Обработка

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

Методика

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.

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