Nitromethane → 3-Nitromethyl-5-(propene-3-yl)cyclopentanone

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 5-(propene-3-yl)cyclopent-2-enone (0.428, 3.5 mmol) in nitromethane (2 mL) under nitrogen was treated with DOWEX® 550A-OH resin (0.80 g, which previously had been rinsed with methanol and partially air dried), and heated to 60° C. for 2 h. The mixture was cooled to room temperature, diluted with methylene chloride (20 mL), and filtered. The filtrate was concentrated in vacuo, redissolved in minimum methylene chloride, and loaded onto a silica gel column (˜100 mL). Elution with methylene chloride afforded the subject compound (0.368 g, 57%) as a colorless oil. NMR (CDCl3): δ 5.65-5.80 (m, 1 H), 5.00-5.15 (m, 2 H), 4.40-4.50 (m, 2 H), 2.85-3.15 (m, 1 H), 2.30-2.70 (m, 4 H), 1.90-2.20 (m, 3 H). MS (M+1): 183.9.

Provenance & Evidence