反应详情

温度

60 °C

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.

1. washpreviously had been rinsed with methanol and partially air
2. customdried), and
3. temperatureThe mixture was cooled to room temperature
4. additiondiluted with methylene chloride (20 mL)
5. filtrationfiltered
6. concentrationThe filtrate was concentrated in vacuo
7. dissolutionredissolved in minimum methylene chloride
8. washElution with methylene chloride