Hydrochloric Acid → HCID 49765928, compound

Participants

Reaction Conditions

Reaction Steps

(2R)-1-Phenyl-2-propanol (0.5 ml, 3.65 mmol) was added dropwise to a solution of p-toluenesulfonyl chloride (0.73 g, 3.83 mmol) in pyridine) (3 ml) at 0° C. The mixture was stirred at 0° C. under nitrogen for 30 minutes then at room temperature overnight. The reaction mixture was poured into 2M hydrochloric acid (75 ml) and extracted with diethyl ether (2×50 ml). The extracts were washed with 2M hydrochloric acid (50 ml), saturated sodium hydrogen carbonate (50 ml) and brine (50 ml), combined, dried (MgSO4) and concentrated in vacuo to give the title compound as a white solid (0.95 g, 90%); δH (250MHz, CDCl3) 1.30 (3H, d, J 6.2Hz, CHCH3), 2.42 (3H, s, ArCH3), 2.77 (1H, dd, J 13.8, 6.6Hz, CH(OTs)CHAHBPh), 2.92 (1H, dd, J 13.8, 6.6Hz, CH(OTs)CHAHBPh), 4.74 (1H, m, CHOTs), 7.03 (2H, m, ArH), 7.20 (5H, m, ArH), 7.62 (1H, m. ArH).

Provenance & Evidence