3-(benzyloxy)-2,2-bis((benzyloxy)methyl)propan-1-ol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A Jones reagent (0.984 mmol) was added to 5 mL of a solution of 3-benzyloxy-2,2-bis(benzyloxymethyl)propan-1-ol (200 mg, 0.492 mmol) obtained in the Step A in acetone under ice-cooling, and the mixture was stirred at room temperature for one hour. Water was added to the mixture, followed by extraction with ethyl acetate. The extract was washed with saturated saline and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 3-benzyloxy-2,2-bis(benzyloxymethyl)propionic acid (206 mg, 100%) as a colorless solid. cooling followed by extraction with ethyl acetate The extract was washed with saturated saline dried over anhydrous sodium sulfate the solvent was evaporated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium hydride (440 mg, 11.01 mmol) and benzyl bromide (1.3 mL, 11.01 mmol) were added to 20 mL of a solution of pentaerythritol (500 mg, 3.67 mmol) in DMF, and the mixture was stirred at room temperature for 14 hours. Aqueous saturated ammonium chloride was added to the mixture, followed by extraction with ethyl acetate. The extract was washed with saturated saline and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain 3-benzyloxy-2,2-bis(benzyloxymethyl)propan-1-ol (560 mg, 38%) as a colorless oil. followed by extraction with ethyl acetate The extract was washed with saturated saline dried over anhydrous sodium sulfate the solvent was evaporated under reduced pressure The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)