Water → rac-1-O-benzyl-2-O-methyl-3-O-tritylglycerol

Participants

Reaction Steps

NaNH2 (0.616 g, 15.0 mmol) was added to a flame-dried two-necked 50 ml round bottom flask equipped with a reflux condenser which contained a solution of rac-1-O-benzyl-3-O-tritylglycerol (5.30 g, 12.5 mmol) in anhydrous 1,4 dioxane (30 ml). The reaction mixture was refluxed for one hour under N2. Then CH3I (3.55 g, 25.0 mmol) was added dropwise. The resulting reaction mixture was refluxed overnight. After the mixture had cooled to room temperature, ether and H2O were added. The ether layer was removed and extracted with 1N HCl, H2O, sat. NaHCO3, H2O, and brine. The organic layer was dried (MgSO4) and the solvent was removed in vacuo to give a yellow oil which solidified upon standing. The crude solid was recrystallized with hexanes to yield pure compound 13, rac-1-O-benzyl-2-O-methyl-3-O-tritylglycerol (4.32 g, 78.9%).

Provenance & Evidence