Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → tert-Butyl 2-(2-(1-(3-hydroxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethoxy)acetate

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 2-(2-(1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethoxy)acetate (1000 mg, 2.24 mmol) and PPTS (169 mg, 0.672 mmol) in MeOH (10 ml) was stirred at 50° C. for 3 h. The reaction was concentrated in vacuo. The crude oil was purified by flash chromatography on SiO2 (0 to 30% EtOAc:hexanes) to afford the title compound (723 mg, 89% yield) as a white solid. LCMS, [M−H]+=361.4. 1H NMR (500 MHz, CDCl3) δ 7.19 (t, J=8.1 Hz, 1H), 6.96-6.91 (m, 2H), 6.71 (ddd, J=8.0, 2.5, 1.0 Hz, 1H), 4.83 (s, 1H), 3.96 (s, 2H), 3.89 (s, 2H), 3.59 (t, J=6.9 Hz, 2H), 2.06-2.00 (m, 4H), 1.78-1.71 (m, 4H), 1.54 (t, J=7.0 Hz, 2H), 1.51 (s, 9H).

Provenance & Evidence