Réaction #2328979

Équation de réaction

water

trans-4-(trans-4-vinylcyclohexyl)cyclohexylmethyl methanesulfonate

2,3-difluoro-4-ethoxyphenol

tripotassium phosphate

→

4-ethoxy-2,3-difluoro-1-(trans-4-(trans-4-vinylcyclohexyl)cyclohexyl)methoxybenzene

Rendement 68.9%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Extractionextracted with toluene
2. 2
   Lavagewashed in turn with water, 10% hydrochloric acid, water, and saturated saline
3. 3
   Séchagedried over anhydrous sodium sulfate
4. 4
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
5. 5
   Autrethe residue was purified in turn
6. 6
   Autreby subjecting to column chromatography (silica gel/toluene), recrystallization (methanol/acetone), column chromatography (alumina/acetone)
7. 7
   Lavagewashing with ion-exchange water, silica treatment, and recrystallization (methanol/acetone)

Mode opératoire

9.8 g of trans-4-(trans-4-vinylcyclohexyl)cyclohexylmethyl methanesulfonate and 5.96 g of 2,3-difluoro-4-ethoxyphenol were dissolved in 90 mL of DMF. 10.4 g of tripotassium phosphate was added, followed by stirring at 90 to 100° C. for 3 hours. The reaction mixture was poured into water, extracted with toluene, washed in turn with water, 10% hydrochloric acid, water, and saturated saline and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified in turn by subjecting to column chromatography (silica gel/toluene), recrystallization (methanol/acetone), column chromatography (alumina/acetone), washing with ion-exchange water, silica treatment, and recrystallization (methanol/acetone) to obtain 8.5 g of 4-ethoxy-2,3-difluoro-1-(trans-4-(trans-4-vinylcyclohexyl)cyclohexyl)methoxybenzene (IIIa) as a colorless crystal.

Source