Benzenepropanal → HCID 9834042, compound

Temperature

-78 °C

A modified procedure of Molander was used (Molander, G. A. et al., The Journal of Organic Chemistry 2009, 74, 1297). A stirred solution of hydrocinnamaldehyde 65 (2.50 g, 2.45 ml, 18.6 mmol) in THF (25 ml) was cooled to −78° C. Vinyl magnesium bromide solution (1 M in THF) (22.4 ml, 22.4 mmol) was added dropwise over ˜5 min. The reaction mixture was stirred at −78° C. for 1.5 h, then 0° C. for 3 h. The reaction mixture was poured into saturated NH4Cl solution (50 ml) and extracted with Et2O (3×50 ml). The combined organic phases were washed with saturated NaCl solution (50 ml) before being dried (MgSO4), filtered and concentrated to give a pale yellow liquid. This material was purified by column chromatography, eluting with petrol/EtOAc (9:1), to give the vinyl alcohol 64 (1.89 g, 63%) as a clear colourless liquid. The 1H, 13C, and IR data were consistent with the literature (Molander, G. A. et al., The Journal of Organic Chemistry 2009, 74, 1297; Kim, J. W. et al., Chemistry—A European Journal 2008, 14, 4104).

1. wait0° C. for 3 h
2. extractionextracted with Et2O (3×50 ml)
3. washThe combined organic phases were washed with saturated NaCl solution (50 ml)
4. dry with materialbefore being dried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated
7. customto give a pale yellow liquid
8. customThis material was purified by column chromatography
9. washeluting with petrol/EtOAc (9:1)

ORD record

ord-0c8f727703f6407997f4f22571a26392

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242954B2