p-Toluenesulfonic acid → HCID 89525931, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1b (1.02 g, 5.49 mmol) and 1,3-propanediol (0.600 mL, 8.23 mmol) in benzene (10.8 mL) was treated with p-toluenesulfonic acid (522 mg, 2.75 mmol). The reaction mixture was stirred at 80° C. for 4.5 h. Saturated aqueous NaHCO3 was added, and the mixture was extracted with Et2O. The organic extract was washed (water), dried (Na2SO4), concentrated to a brown liquid, and chromatographed [silica, hexanes/EtOAc (5:1)] to afford a yellow liquid (600 mg, 64%): 1H NMR δ 1.40-1.45 (m, 1H), 1.96 (s, 3H), 2.20 (s, 3H), 2.12-2.25 (m, 1H), 3.83-3.92 (m, 2H), 4.20-4.26 (m, 2H), 4.79 (s, 1H), 6.42 (s, 1H); 13C NMR δ 21.7, 25.9, 28.5, 67.3, 101.4, 119.0, 161.2, 192.1; ESI-MS obsd 193.0833, calcd 193.0835 [(M+Na)+, M=C9H14O3].

Provenance & Evidence