Реакция #5399

Уравнение реакции

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

3,4-dihydro-2H-pyran

bistrimethylsilyl sulfate

→

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

Растворители

dichloromethane

dichloromethane

Условия реакции

Обработка

1. 1
   Промывкаwashed once with sodium carbonate solution and twice with water
2. 2
   Сушкаsubsequently dried over magnesium sulfate
3. 3
   Фильтрацияfiltered
4. 4
   Концентрированиеconcentrated
5. 5
   ДругоеThe crude product was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1)
6. 6
   ДругоеRecrystallization from ethyl acetate at -20° C.

Методика

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.

Источник