Reaction #1183032
Related Literature (1)
openreactiondata ↗doi:10.6084/m9.figshare.5104873.v1; patent:US06071928
Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: (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). at room temperature overnight 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) dried (MgSO4) concentrated in vacuo
Source ID: ord-d9b1eb6ffaf249d2a76a3ef5f70f6610