[BMIM][AlCl4] T=25°C; 0.5 h;

cerium(III) chloride in methanol T=20°C; detetrahydropyranylation; 1 h;

[BMIM][AlCl4] T=25°C; 0.5 h;

pyridinium p-toluenesulfonate in dichloromethane T=20°C; 4 h;

sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride in ethanol 4 h; Yields of byproduct given;

1: 72 percent / 50percent aqueous sodium hydroxide / benzyltriethylammonium chloride / ethanol / 4 h 2: 90 percent / 1 N hydrochloric acid / methanol / Ambient temperature View Scheme

1: 50percent aqueous sodium hydroxide / benzyltriethylammonium chloride / ethanol / 4 h 2: 1.) pyridium chlorochromate, 2.) basic alumina column / 1.) dichloromethane, room temp., 2 h. 3: 1.) n-butyllithium / 1.) THF, -78 deg C -> room temp., 30 min., 2.) THF, room temp., 1 h. View Scheme