Reaction #1960499

Reaction equation

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

Solvents

water

THF

THF

Conditions

Workup

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

Procedure

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