4-Methylmorpholine → HCID 54456794, compound

Participants

Reaction Steps

At 0° C. to a solution of 708 mg (3.54 mmol) of 4-benzylresorcinol in 20 mL of methylene chloride at 0° C. was added 410 μL (3.72 mmol) of N-methylmorpholine followed by 740 mg (3.51 mmol) of 2-chlorobenzenesulfonyl chloride. The reaction mixture was warmed to ambient temperature and stirred for 30 min. An additional 400 μL of N-methylmorpholine was added and the reaction mixture was stirred for another 60 min. The reaction mixture was quenched with 1N HCl, extracted into ether, washed with saturated NaHCO3, dried (MgSO4), and purified by flash chromatography (methylene chloride) to give 336.5 mg (25%) of the title compound as a colorless oil. 1H-NMR (300 MHz, CDCl3) δ 7.95 (dd, 1H, J=1, 8 Hz), 7.55-7.63 (m, 2H), 7.34-7.40 (m, 1H), 7.1-7.3 (m, 5H), 6.98 (d, 1H), 6.61-6.65 (m, 2H), 4.95 (s, 1H), and 3.91 (s, 2H). Mass spectrum (MALDI-TOF; gentisic acid matrix) calcd. for C19H15ClO4S: 375.0 (M+H), 397.0 (M+Na). Found: 373.6, 396.7.

Provenance & Evidence