반응 #1960506

반응 방정식

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

용매

water

THF

반응 조건

후처리

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

실험 절차

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.

출처