p-Toluenesulfonic acid → HCID 15229847, compound

Participants

Reaction Steps

To a stirred suspension of the alcohol from example 2 above (310 mg, 0.7 mmol) in toluene (8 ml )was added p-toluene sulfonic acid (200 mg). This was boiled without a condenser until the reaction mixture was a gum. It was then cooled to r.t., sat. NaHCO3 (1 00 ml ) and EtOAc (1 00 ml ) were added. The biphasic mixture was stirred at r.t until all of the gummy solid dissolved. The layers were separated and the organic phase was dried over Na2SO4 and evaporated under reduced pressure to give 166 mg of a pale yellow oil, 55.8%.1H NMR (CDCl3)δ7.28-6.79 (m, 7H), 6.30 (d, J=1OHz, 1H), 5.55 (d, J=10 Hz, 1H), 3.83 (s, 2H), 2.91 (s, 7H), 2.62-2.48 (m, 1H), 2.20 (d, J=12 Hz, 2H), 2.00-1.82 (m, 4H), 1.45 (dt, J=13 Hz, J=4 Hz, 2H).

Provenance & Evidence