Reaktion #5401

Reaktionsgleichung

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

bistrimethylsilyl sulfate

pyridine

→

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

Ausbeute 50.6%

Lösungsmittel

methanol

diethyl ether

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenSubseguently, the reaction mixture was concentrated
2. 2
   Waschenwashed twice with water
3. 3
   Trocknendried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenagain concentrated
6. 6
   SonstigeThe residue was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1)
7. 7
   SonstigeRecrystallization from methanol

Vorschrift

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.

Quelle