Réaction #1960499

Équation de réaction

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

Solvants

water

THF

THF

Conditions de réaction

Traitement

1. 1
   Températurecooling
2. 2
   Extractionthe mixture is extracted a number of times with MTBE
3. 3
   LavageThe combined organic phases are washed with water and saturated sodium chloride soln
4. 4
   Autre, and the solution is dried
5. 5
   Autreafter removal of the solvents
6. 6
   Autreis purified by column chromatography (SiO2, n-heptane MTBE=2:1)

Mode opératoire

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.

Source