Acrolein → HCID 12271754, compound

Temperature

-43 °C

To a stirred solution of furan (9) (15 mL, 200 mmol) and acrolein (13) (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 sat. aq. 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 sat. aq. K2CO3 (200 mL×2) and sat. aq. 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 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.

1. customat −43° C.
2. customquenched with sat. aq. K2CO3 (50 mL)
3. temperatureAfter the reaction mixture was gradually warmed to room temperature
4. extractionit was extracted with ether (200 mL×5)
5. washThe combined ether extracts were washed with sat. aq. K2CO3 (200 mL×2) and sat. aq. NaCl (200 mL×2)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-484f0adf3deb44568a38217cdac6452c

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07786141B2