Reaktion #1960506

Reaktionsgleichung

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

Lösungsmittel

water

THF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle