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, δ 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-a4ee26a5bb5c47e1bb03e908b3980bac

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07354934B2