反応 #1960499

反応方程式

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

溶媒

water

THF

THF

反応条件

後処理

1. 1
   温度cooling
2. 2
   抽出the mixture is extracted a number of times with MTBE
3. 3
   洗浄The combined organic phases are washed with water and saturated sodium chloride soln
4. 4
   その他, and the solution is dried
5. 5
   その他after removal of the solvents
6. 6
   その他is purified by column chromatography (SiO2, n-heptane MTBE=2:1)

実験手順

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.

出典