Reaktion #89691

Reaktionsgleichung

M−H2O

H2O

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

benzyl carbamate

bismuth trinitrate pentahydrate

→

benzyl 3-allyl-4-oxocyclopentylcarbamate

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe mixture was filtered through Celite® (rinse with dichloromethane)
2. 2
   workup.ADDITIONthe filtrate added directly to a silica gel column (˜550 cc)
3. 3
   WaschenElution first with 3:2 petroleum ether/dichloromethane
4. 4
   Sonstigeafforded
5. 5
   Sonstigerecovered
6. 6
   Sonstige4:1 heptane/ethyl acetate gave
7. 7
   Sonstigethe subject compound (4.54 g, 47.5% uncorrected yield) as a pale yellow oil

Vorschrift

A solution of 5-(propene-3-yl)cyclopent-2-enone (4.28 g, 35 mmol) in dichloromethane (15 mL) was treated with benzyl carbamate (10.6 g, 70 mmol) and bismuth trinitrate pentahydrate (2.2 g, 4.5 mmol), stirred rapidly for 18 h, then diluted with dichloromethane (50 mL). The mixture was filtered through Celite® (rinse with dichloromethane) and the filtrate added directly to a silica gel column (˜550 cc). Elution first with 3:2 petroleum ether/dichloromethane afforded recovered starting material (1.01 g), then 4:1 heptane/ethyl acetate gave the subject compound (4.54 g, 47.5% uncorrected yield) as a pale yellow oil. NMR (CDCl3): δ 7.28 (br s, 5 H), 5.55-5.70 (m, 1 H), 5.03 (br s, 2 H), 4.90-5.10 (m, 2 H), 4.75-4.90 (m, 1 H), 4.10-4.30 (m, 1 H), 2.40-2.80 (m, 2 H), 2.15-2.40 (m, 2 H), 1.85-2.15 (m, 3 H). MS (M+Na): 296.0; MS (M−H2O+1): 256.0 (no M+1 visible).

Quelle