反応 #1960506

反応方程式

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

溶媒

water

THF

反応条件

後処理

1. 1
   workup.ADDITIONare added over the course of 20 min with ice-
2. 2
   温度cooling
3. 3
   抽出the mixture is extracted a number of times with MTBE
4. 4
   洗浄The combined organic phases are washed with water and saturated sodium chloride soln
5. 5
   その他, and the solution is dried
6. 6
   その他after removal of the solvents
7. 7
   その他is purified by column chromatography (SiO2, n-heptane:MTBE=2:1)
8. 8
   その他The further purification
9. 9
   その他is carried out by recrystallisation from n-heptane

実験手順

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.

出典