Triethylamine → HCID 10866837, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of the above alcohol (43) (0.13 g, 0.83 mmol) in dry CH2Cl2 (5 mL) at 0° C. was treated with methanesulfonyl chloride (0.36 mL. 1.25 mmol), followed by Et3N (0.50 mL). After stirring at 0° C. for 15 min, the mixture was evaporated to dryness under reduced pressure at room temperature, and the resulting brown solid was partitioned between water and EtOAc. Workup of the organic layer gave a crude product which was was chromatographed on silica gel. Elution with CH2Cl2 /petroleum ether (1:1) gave 1-methyl-2-chloromethyl-5-nitropyrrole (44) (0.13 g, 88%), mp (EtOAc/petroleum ether) 82.5-83.5° C. 1H NMR (CDCl3) δ 7.16 (d, J=4.4 Hz, 1 H, H-4), 6.26 (d, J=4.4 Hz, 1 H, H-3), 4.60 (s, 2 H, CH2Cl), 4.02 (s, 3 H, CH3). Anal. Calculated for C6H7ClN2O2 : C, 41.3; H, 4.0; N, 16.0. Found: C, 41.4; H, 4.0; N, 15.9%.

Provenance & Evidence