Benzaldehyde → 2-Benzylidene-3-quinuclidinone

Participants

Reaction Steps

To quinuclidine-3-one hydrochloride (Aldrich Chemical Co.) (49.9 g) in water (200 ml) was added sodium hydroxide (12.5 g, 0.310 mol). The aqueous layer was extracted with dichloromethane (2×200 ml) and the combined organic layers dired (Na2CO3), filtered, and evaporated in vacuo to give a colourless oil. The oil (38.64 g) was dissolved in ethanol (400 ml) and sodium hydroxide (3 g) added, followed by benzaldehyde (32.8 g). The reaction mixture was heated at reflux for 2 h. On cooling the product crystallized from the solution as a yellow solid. 1H NMR (CDCl3) δ 1.96-2.08 (4H, m), 2.62-2.66 (1H, m), 2.92-3.24 (4H, m), 7.02 (1H, s), 7.32-7.42 (3H, m), 8.00-8.04 (2H, m).

Provenance & Evidence