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-87e33ee7817045079ecd600981efbb1d

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367691B2