Iodoethane → HCID 22498573, compound

Temperature

60 °C

Ethyl iodide (64 mL, 0.796 mol) was added to furylacrylic acid (100 g, 0.724 mol), diisopropylethyl amine (140 mL, 0.796 mmol), in acetonitrile (1100 mL), and the mixture was heated to 60° C. After 18 h, the dark solution was cooled to room temperature and concentrated in vacuo. The resulting brown sludge was diluted with Et2O (500 mL), washed with 1 N aqueous HCl (2×250 mL), washed with 0.2 N aqueous NaOH (2×250 mL), washed with saturated aqueous NaH.CO3 (1×250 ML), dried (MgSO4), filtered, and concentrated to a black oil (114 g, 95%). 1H NMR (DMSO-d6, 300 MHz) δ 7.84 (d, J=1.7 Hz, 1H), 7.46 (d, J=15.6 Hz, 1H), 6.97 (d, J=3.4 Hz, 1H), 6.33 (dd, J=3.4 Hz, J=1.7 Hz, 1H), 6.22 (d, J=15.9 Hz, 1H), 4.17 (q, J=7.1 Hz, 2H), 1.24 (t, J=7.1 Hz, 3H); MS (APCI) m/z 167 (M+H)+.

1. temperaturethe dark solution was cooled to room temperature
2. concentrationconcentrated in vacuo
3. additionThe resulting brown sludge was diluted with Et2O (500 mL)
4. washwashed with 1 N aqueous HCl (2×250 mL)
5. washwashed with 0.2 N aqueous NaOH (2×250 mL)
6. washwashed with saturated aqueous NaH
7. dry with materialCO3 (1×250 ML), dried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated to a black oil (114 g, 95%)

ORD record

ord-ff54e552bb4741da9bbac62949e605dc

Source dataset

uspto-grants-2005_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06867203B2