Ethyl Acrylate → 3-Benzofuran-6-yl-acrylic acid ethyl ester

Temperature

100 °C

A mixture of the 6-bromo-benzofuran 1-3 (1.74 g, 8.79 mmol), ethyl acrylate (1.09 g, 10.98 mmol), Pd(OAc)2 (0.099 g, 0.44 mmol), tri-o-tolylphosphine (0.268 g, 0.880 mmol), and sodium acetate (3.60 g, 43.9 mmol) in DMF (10 mL) was heated to 100° C. in a sealed tube for 4 h. The mixture was cooled to room temperature, diluted with water, and extracted with Et2O (2×40 mL). The combined organic extracts were washed with brine (30 mL), dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (10% ethyl acetate/hexanes) to give the ester 1-4 as an off-white solid. TLC Rf=0.3 (10% ethyl acetate/hexanes). 1H NMR (300 MHz, CDCl3) δ 7.78 (d, 1H, J=15.9 Hz), 7.68 (d, 1H, J=2.4 Hz), 7.66 (s, 1H), 7.59 (d, 1H, J=8.4 Hz), 7.43 (dd, 1H, J=9.0, 1.5 Hz), 6.78 (m, 1H), 6.47 (d, 1H, J=15.9 Hz), 4.27 (q, 2H, J=7.2 Hz), 1.34 (t, 3H, J=7.2 Hz).

1. temperatureThe mixture was cooled to room temperature
2. extractionextracted with Et2O (2×40 mL)
3. washThe combined organic extracts were washed with brine (30 mL)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue was purified by flash chromatography (10% ethyl acetate/hexanes)

ORD record

ord-88be7648c2cc4d388f99d9e1b3e232c6

Source dataset

uspto-grants-2000_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06017926