Triethylamine → N-(2-allyl-4-fluoro-phenyl)-acrylamide

Temperature

-10 °C

A round-bottom flask containing the product from Step 1 (10.6 g, 70.1 mmol) was fitted with a stirbar and septa. Tetrahydrofuran (200 mL) and triethylamine (15.0 mL, 108 mmol) were added, giving a solution that was cooled to −10° C. Acryloyl chloride (6.0 mL, 73.6 mmol) was then added, and the resulting mixture was allowed to gradually warm to room temperature. After 16 hours, the reaction was concentrated to remove most of the tetrahydrofuran, then diluted with ethyl acetate (200 mL) and washed with 1:1 H2O:saturated aqueous NaCl solution (2×100 mL). The organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give an oil which was purified via flash chromatography on silica gel (15% to 40% ethyl acetate/hexanes linear gradient) to give the desired product.

1. customwas fitted with a stirbar and septa
2. customgiving a solution that
3. temperatureto gradually warm to room temperature
4. concentrationthe reaction was concentrated
5. customto remove most of the tetrahydrofuran
6. additiondiluted with ethyl acetate (200 mL)
7. washwashed with 1:1 H2O
8. dry with materialThe organic extracts were dried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customto give an oil which
12. customwas purified via flash chromatography on silica gel (15% to 40% ethyl acetate/hexanes linear gradient)

ORD record

ord-703af0ac406b446c9b31ebe47061b457

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07888345B2