Réaction #5399

Équation de réaction

trans-4-(4'-cyano-4-biphenylyl)cyclohexanol

3,4-dihydro-2H-pyran

bistrimethylsilyl sulfate

→

trans-4-(4'-cyano-4-biphenylyl)cyclohexyl tetrahydropyranyl ether

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   Lavagewashed once with sodium carbonate solution and twice with water
2. 2
   Séchagesubsequently dried over magnesium sulfate
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated
5. 5
   AutreThe crude product was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1)
6. 6
   AutreRecrystallization from ethyl acetate at -20° C.

Mode opératoire

A solution of 3.0 g of trans-4-(4'-cyano-4-biphenylyl)cyclohexanol, 1.1 ml of 3,4-dihydro-2H-pyran in 30 ml of dichloromethane was treated at 0° C. with a solution of 0.007 g of bistrimethylsilyl sulfate in 2 ml of dichloromethane. The reaction mixture was stirred at 0° C. for a further 30 minutes and then washed once with sodium carbonate solution and twice with water and subsequently dried over magnesium sulfate, filtered and concentrated. The crude product was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1). Recrystallization from ethyl acetate at -20° C. gave 1.75 g of pure trans-4-(4'-cyano-4-biphenylyl)cyclohexyl tetrahydropyranyl ether.

Source