反応 #5399

反応方程式

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

3,4-dihydro-2H-pyran

bistrimethylsilyl sulfate

→

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

溶媒

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   洗浄washed once with sodium carbonate solution and twice with water
2. 2
   乾燥subsequently dried over magnesium sulfate
3. 3
   ろ過filtered
4. 4
   濃縮concentrated
5. 5
   その他The crude product was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1)
6. 6
   その他Recrystallization from ethyl acetate at -20° C.

実験手順

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.

出典