Reacción #5401

Ecuación de reacción

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

bistrimethylsilyl sulfate

pyridine

→

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

Rendimiento 50.6%

Disolventes

methanol

diethyl ether

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónSubseguently, the reaction mixture was concentrated
2. 2
   Lavadowashed twice with water
3. 3
   Secadodried over magnesium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónagain concentrated
6. 6
   OtroThe residue was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1)
7. 7
   OtroRecrystallization from methanol

Procedimiento

A solution of 1.2 g of trans-4-(4'-decyl-4-biphenylyl)cyclohexyl tetrahydropyranyl ether in 40 ml of methanol and 2 ml of diethyl ether was treated with a solution of 7.3 mg of bistrimethylsilyl sulfate in 2 ml of dichloromethane. The reaction mixture was stirred at room temperature for 2 hours and then treated with 0.2 ml of pyridine. Subseguently, the reaction mixture was concentrated and the residue was then taken up in 50 ml of dichloromethane, washed twice with water, dried over magnesium sulfate, filtered and again concentrated. The residue was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1). Recrystallization from methanol gave 0.5 g of trans-4-(4'-decyl-4-biphenylyl)cyclohexanol.

Fuente