HCID 66912107, compound → HCID 58706352, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-ethoxy-6-hydroxymethyl-3H-benzooxazol-2-one (0.69 g, 3.30 mmol, 1.0 equiv) in a mixture of dichloromethane (40 mL) and ethanol (5 mL) was added activated MnO2 (1.15 g, 13.2 mmol, 4.0 equiv). The reaction mixture was heated to 40° C. for 2 h, filtered through Hyflo Super Cel and concentrated by evaporation under reduced pressure. The residue was purified by flash column chromatography on silica eluting with heptane/ethyl acetate (1:1) to yield 0.53 g (78% yield) of the title compound. 1H NMR (300 MHz, DMSO): δ 1.43 (t, J=7.0 Hz, 3H), 4.23 (q, J=7.0 Hz, 2H), 7.38 (s, 1H), 7.42 (s, 1H), 9.87 (s, 1H), 12.28 (br s, 1H). 13C NMR (75 MHz, DMSO): δ 14.41, 64.63, 104.07, 109.32, 125.20, 131.05, 143.13, 143.88, 154.21, 191.11. MS (ISP): 208.1 [M+H]+.

Provenance & Evidence