4-Toluenesulfonyl chloride → HCID 57522713, compound

Participants

Reaction Steps

Et3N (34.7 mg, 0.343 mmol), CH3COOAg (57.2 mg, 0.343 mmol), and TsCl (65.4 mg, 0.343 mmol) were added to the solution of 18 (50 mg, 0.172 mmol) in CH2Cl2 (50 mL). The reaction mixture was stirred at room temperature for 16 h, and then washed with sat. NaHCO3 (50 mL) and brine (50 mL). The organic layer was dried over Na2SO4, filtered and concentrated, adsorbed onto SiO2, and purified by flash column chromatography (SiO2), eluting with EtOAc-CHCl3 (2:8) to afford the desired product as a red solid (38.5 mg, 67%): mp 221-224° C. IR (film) 1738, 1693, 1655, and 1506 cm−1; 1H NMR (300 MHz, CDCl3) δ 8.75 (d, J=8.0 Hz, 1 H), 8.37 (d, J=7.9 Hz, 1 H), 7.75 (t, J=5.8 Hz, 2 H), 7.67 (dd, J=1.1 and 5.8 Hz, 1 H), 7.51-7.41 (m, 3 H), 4.84 (t, J=6.2 Hz, 2 H), 4.57 (t, J=6.1 Hz, 2 H), 1.94 (s, 3 H)); probe-EI/CI-MS m/z (rel intensity) 334 (MH+, 100); HRMS (+EI/CI) calcd for M+: 333.1001, found: 333.1005; HPLC purity: 97.3% (MeOH, 100%), 98.0% (MeOH—H2O, 90:10).

Provenance & Evidence