methyl 4-(hydroxymethyl)oxane-4-carboxylate

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

Procedure: Under an atmosphere of argon, to a solution of lithium aluminum tri(tert-butoxy)hydride (1.93 g) in tetrahydrofuran (15 mL) was added a solution of dimethyl tetrahydro-2H-pyran-4,4-dicarboxylate (606 mg) in tetrahydrofuran (5 mL) and the mixture was stirred at room temperature for an hour. To the reaction mixture was added an an aqueous saturated sodium sulfate solution till being cloudy. An insoluble matter was filtered and the filtrate was concentrated. The obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1→1:2→1:4→ethyl An insoluble matter was filtered the filtrate was concentrated The obtained residue was purified by column chromatography on silica gel (hexane