Methanol → HCID 22221005, compound

Participants

Reaction Steps

A mixture of 3-[5-(3-bromo-4-fluorophenyl)-4-isoxazolyl]propionic acid (2.38 g), conc. sulfuric acid (0.1 ml) and methanol (100 ml) was refluxed for 4 hr. The reaction mixture was concentrated, water was added to the residue and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and methyl 3-[5-(3-bromo-4-fluorophenyl)-4-isoxazolyl]propionate (2.39 g, yield 96%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (1:3, volume ratio). NMR (CDCl3) δ: 2.60–2.71 (2H, m), 2.91–3.03 (2H, m), 3.69 (3H, s), 7.18–7.32 (1H, m), 7.60–7.70 (1H, m), 7.94 (1H, dd, J=2.2, 6.2 Hz), 8.23 (1H, s).

Provenance & Evidence