Acrolein → HCID 12271754, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of furan (C1) (15 mL, 200 mmol) and acrolein (6.7 mL, 100 mmol) in DCM (25 mL) was slowly added AlCl3 (666 mg, 5 mmol) under argon at −43° C. (dry ice/isopropanol bath). The reaction mixture was stirred at −43° C. under argon for 30 min and then quenched with saturated aqueous K2CO3 (50 mL). After the reaction mixture was gradually warmed to room temperature, it was extracted with ether (200 mL×5). The combined ether extracts were washed with saturated aqueous K2CO3 (200 mL×2) and saturated aqueous NaCl (200 mL×2), dried over MgSO4, filtered, and concentrated to give an oily crude product, 7-oxa-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde (C2), which was used in the next step without further purification. See references Laszlo, P.; Lucchetti, J. Tetrahedron Lett. 1984, 25, 4387-4388. Moore, J. A., Partain, E. M. III. J. Org. Chem. 1983, 48, 1105-1106. Dauben, W. G.; Krabbenhoft, H. O. J. Am. Chem. Soc. 1976, 98, 1992-1993. Nelson, W. L.; Allen, D. R.; Vincenzi, F. F. J. Med. Chem. 1971, 14, 698-702.

Provenance & Evidence