Potassium Carbonate → ethyl 3-hydroxy-3,6-dihydro-2H-pyran-4-carboxylate

Participants

Reaction Steps

To an aqueous solution (400 mL) of (3R,4S)-tetrahydrofuran-3,4-diol (100 g) was added sodium periodate (225 g) at 0° C., and the mixture was stirred at room temperature for 1 hr. An aqueous solution (50 mL) of potassium carbonate (13.2 g) was added at room temperature, and an aqueous solution (100 mL) of ethyl diethylphosphonoacetate (322 g) was added dropwise over 2 hr. Then, an aqueous solution (800 mL) of potassium carbonate (384 g) was added dropwise over 2 hr. The reaction mixture was stirred at room temperature for 24 hr, and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was distilled under reduced pressure (110-130° C./3-4 mmHg). The obtained crude product was subjected to silica gel column chromatography (hexane/ethyl acetate=1:1) to give the title compound (66.5 g, 40%) as a colorless liquid.

Provenance & Evidence