Water → Oxane-2-carboxylic acid

Participants

Reaction Steps

To a vigorously stirred solution of tetrahydropyran-2-methanol (2.32 g, 40 mmol) in a mixture of CH3CN (20 ml), CCl4 (20 ml) and water (10 ml) at 0° C. was added NaIO4 (9.42 g, 44 mmol) and then RuCl3H2O(414 mg, 2 mmol). After 20 min, the cooling bath was removed. After 40 min at room temperature, TLC showed reaction was complete. The reaction mixture was partitioned into ethyl acetate and ice-cold Na2S2O5 solution. More Na2S2O5 was added until all the brown material dissolved and a greenish mixture was obtained. The aqueous portion was extracted with more ethyl acetate and combined layer was washed with 10% Na2S2O5, H2O, brine, dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography using methylene chloride/methanol/acetic acid=95:5:0.5 to afford the product as an oil (1.5 g).

Provenance & Evidence