p-Toluenesulfonic acid → Methyl 2-(1-(3-hydroxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)acetate

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(1-(3-hydroxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)acetic acid (910 mg, 3.47 mmol) and p-TsOH (66 mg, 0.347 mmol) in MeOH (10 mL) was stirred at 60° C. for 18 h. The reaction was concentrated in vacuo. The crude oil was purified by flash chromatography on SiO2 (0 to 50% EtOAc:hexanes) to afford the title compound (887 mg, 93% yield) as a clear oil. LCMS, [M+H]+=277.3. 1H NMR (500 MHz, CDCl3) δ 7.13 (t, J=7.9 Hz, 1H), 6.93-6.84 (m, 2H), 6.69-6.63 (m, 1H), 6.13 (s, 1H), 3.94 (s, 2H), 3.67 (s, 3H), 2.18 (s, 2H), 2.06-1.94 (m, 4H), 1.86-1.72 (m, 4H).

Provenance & Evidence