Diethyl Ether → Tetrahydropyranyl ether
Reaction equation
[Si](O[C@H:9]1[CH2:13][C@@H:12]([OH:14])[CH:11]=[CH:10]1)(C(C)(C)C)(C)C.[O:15]1[CH:20]=[CH:19][CH2:18][CH2:17][CH2:16]1.CC[O:23]CC>C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]1[O:23][CH:12]1[CH2:13][CH2:9][CH2:10][CH2:11][O:14]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of (1R,4S)-4-(tert-butyldimethylsilyl)oxy-2-cyclopentenol (9.70 g, 40 mmol) (J. Amer. Chem. Soc., 1991, 113, 9851,), dihydropyran (4.40 g, 53.0 mmol) and p-toluenesulfonic acid (100 mg) in dry ether (50 ml) was stirred for 10 h at room temperature. The reaction mixture was washed with saturated aqueous sodium hydrogen carbonate solution (50 ml) and brine (50 ml). The organic phase was dried (MgSO4) and concentrated under reduced pressure to afford 14.2 g of crude tetrahydropyranyl ether of (1R,4S)-4-(tert-butyldimethylsilyl)oxy-2-cyclopentenol as a colorless oil.