p-Toluenesulfonic acid → HCID 11119733, compound

Participants

Reaction Steps

To a solution of 2-5 (35 g, 0.1 mol) in 600 mL acetone was added p-toluenesulfonic acid (1 g). The mixture was heated at reflux for 2 h. After cooling, the mixture was evaporated to one-fifth its initial volume, diluted with EtOAc and then washed with sat. NaHCO3, brine, and dried over Na2SO4. Evaporative removal of the solvent gave 2-6 as a yellow oil. TLC Rf =0.31 (silica, 30% ethyl acetate/hexane). 1H NMR (300 MHz, CDCl3, mixture of rotamers) δ 4.20 (m, 2H), 3.92 (s, 0.85H), 3.83 (s, 1.15 H), 3.3 (m, 2H), 2.52 (m, 2H), 2.14 (s, 3H), 1.78 (m, 2H), 1.51-1.42 (3s, 9H), 1.28 (m, 3H).

Provenance & Evidence