Reaktion #89693

Reaktionsgleichung

5-(propene-3-yl)cyclopent-2-enone

nitromethane

→

compound

Ausbeute 57.0%

2-allyl-4-(nitromethyl)cyclopentanone

Ausbeute 57.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenrinsed with methanol and partially air
2. 2
   Sonstigedried), and
3. 3
   TemperaturThe mixture was cooled to room temperature
4. 4
   workup.ADDITIONdiluted with dichloromethane (20 mL)
5. 5
   Filtrationfiltered
6. 6
   EinengenThe filtrate was concentrated in vacuo
7. 7
   workup.DISSOLUTIONredissolved in minimum dichloromethane
8. 8
   workup.ADDITIONadded to a silica gel column (˜100 cc)
9. 9
   Wascheneluted with dichloromethane

Vorschrift

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, rinsed with methanol and partially air dried), and heated to 60° C. for 2 h. The mixture was cooled to room temperature, diluted with dichloromethane (20 mL), and filtered. The filtrate was concentrated in vacuo, redissolved in minimum dichloromethane, and added to a silica gel column (˜100 cc) and eluted with dichloromethane to afford 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.

Quelle