Water → HCID 10538577, compound

Participants

Reaction Conditions

Reaction Steps

Benzenesulfonyl chloride (12.9 mL, 101 mmol, 1.10 equiv) was added to a stirred solution of 5-hydroxy-2-methylpyridine (10.0 g, 91.6 mmol, 1 equiv) and triethylamine (15.3 mL, 110 mmol, 1.20 equiv) in dichloromethane (100 mL) at 0° C. After stirring for 2 h at 0° C., water (20 mL) was added and the resulting two-phase mixture was stirred vigorously for 1 h at 23° C. to quench any remaining sulfonyl chloride. Saturated aqueous potassium carbonate solution (100 mL) was added and the layers were separated. The aqueous layer was extracted with a second portion of dichloromethane (150 mL). The combined organic layers were dried over anhydrous potassium carbonate, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with a gradient of 4:1 to 1:1 of hexane and ethyl acetate to provide 4 (21.8 g, 95%) as an oil. Chromatography may be avoided by using exactly one equivalent of benzenesulfonyl chloride to afford product of sufficient purity for direct submission to benzylic bromination conditions (see below). IR (neat) 3066, 1594, 1480, 1450, 1384, 1286, 1204, 1177, 1093, 1024, 865, 837, 804, 757, 741, 724, 692; 1H NMR (CDCl3) 8.01(d, 1H, J=2.7), 7.84 (d, 2H, J=7.9), 7.70 (t, 1H, J=7.2), 7.55 (t, 2H, J=7.8), 7.33 (dd, 1H, J=8.5, 2.7), 7.13 (d, 1H, J=8.5), 2.53 (s, 3H). Anal. Calcd. for C12H11NO3S: C, 57.82; H, 4.45; N, 5.62. Found C, 57.66; H, 4.33; N, 5.47.

Provenance & Evidence