Реакция #1960499

Уравнение реакции

DIAD

3,4-difluoro-6-(4-propylcyclohexyl)-5,6,7,8-tetrahydronaphthalen-2-ol

1-hexyn-3-ol

triphenylphosphine

→

6-(1-ethynylbutoxy)-7,8-difluoro-2-(4-propylcyclohexyl)-1,2,3,4-tetrahydronaphthalene

Растворители

water

THF

THF

Условия реакции

Обработка

1. 1
   Температураcooling
2. 2
   Экстракцияthe mixture is extracted a number of times with MTBE
3. 3
   ПромывкаThe combined organic phases are washed with water and saturated sodium chloride soln
4. 4
   Другое, and the solution is dried
5. 5
   Другоеafter removal of the solvents
6. 6
   Другоеis purified by column chromatography (SiO2, n-heptane MTBE=2:1)

Методика

7.0 g (22.7 mmol) of 3,4-difluoro-6-(4-propylcyclohexyl)-5,6,7,8-tetrahydronaphthalen-2-ol are initially introduced in 90 ml of THF together with 2.70 ml (24.0 mmol) of 1-hexyn-3-ol and 6.60 g (25.2 mmol) of triphenylphosphine. 5.3 ml (46.8 mmol) of DIAD in 10 ml of THF are added over the course of 20 min with ice-cooling. After 19 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), giving 6-(1-ethynylbutoxy)-7,8-difluoro-2-(4-propylcyclohexyl)-1,2,3,4-tetrahydronaphthalene as a colourless solid.

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