Allyl bromide → HCID 11389413, compound

A solution of 2-imidazole carboxaldehyde (15.0 g, 156 mmol), allyl bromide (22.6 g, 187 mmol) and diisopropylethylamine (40.7 mL, 234 mmol) was stirred in N,N-dimethylformamide (500 mL) for 23 hours. The solvent was removed under reduced pressure and the residue was dissolved in dichloromethane (370 mL). The solution was washed once with a saturated solution of sodium carbonate (185 mL). The layers were separated and the aqueous layer was extracted with dichloromethane (2×280 mL). The combined organic portions were dried with sodium sulfate, filtered and concentrated under reduced pressure to afford a yellow oil. The crude material was then purified by flash chromatography (99:1 CH2Cl2/methanol) to provide the desired compound (12.8 g, 60%) as yellow oil. 1H NMR (300 MHz, CDCl3, δ ppm) 5.04 (d, 2H, J=5.5 Hz), 5.11 (d, 1H, J=17.5 Hz), 5.25 (d, 1H, J=10.0 Hz), 5.90-6.05 (m, 1H), 7.16 (s, 1H), 7.30 (s, 1H), 9.81 (s, 1H); 13C NMR (75 MHz, CDCl3, ppm) 49.77, 118.61, 126.00, 131.74, 132.39, 143.17, 182.05.

1. customThe solvent was removed under reduced pressure
2. dissolutionthe residue was dissolved in dichloromethane (370 mL)
3. washThe solution was washed once with a saturated solution of sodium carbonate (185 mL)
4. customThe layers were separated
5. extractionthe aqueous layer was extracted with dichloromethane (2×280 mL)
6. dry with materialThe combined organic portions were dried with sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customto afford a yellow oil
10. customThe crude material was then purified by flash chromatography (99:1 CH2Cl2/methanol)

ORD record

ord-352cad1953344aa4a0855e1a221a18c5

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778967B2