Acryloyl chloride → HCID 15638264, compound

Temperature

0 °C

A solution of acryloyl chloride (3 mL; 3.342 g; 36.9 mmole) dissolved in dry dichloromethane (25 mL) was cooled at 0° C. with an ice bath. A mixture of O-benzyl hydroxylamine hydrochloride (6.4902 g; 40.66 mmole) and N,N-diisopropylethylamine (15.6 mL; 11.575 g; 89.56 mmole) in dry dichloromethane (110 mL) was slowly added over a period of 1 hour to the cooled solution. Next, the ice bath was removed, and the reaction mixture was left stirring overnight while its temperature warmed up gradually to room temperature. Water (250 mL) was added to the reaction and the layers were separated. The organic solution was washed with diluted hydrochloric acid (0.2N; 3×300 mL), a saturated sodium bicarbonate solution (1×200 mL), water (3×250 mL), and finally brine (1×250 mL). The organic layer was then dried over magnesium sulfate, filtered, and the solvent removed under reduced pressure. The residue was purified by flash chromatography using a mixture of hexane and ethyl acetate (70:30) to elute the product. The purification gave 3.165 g (48.4%) of N-benzyloxyacrylarnide (30) as a viscous colorless oil. 1H NMR (CDCl3; 300 MHz): 8.27 (bs, 1H, C6H5CH2ONHCOCH═CH2), 7.39 (s, 5H, C6H5CH2ONHCOCH═CH2), 6.41 (d, 1H, J=16.6 Hz, C6H5CH2ONHCOCH═CHtrans), 6.02 (m, 1H, C6H5CH2ONHCOCH═CH2), 5.72 (d, 1H, J=9.5 Hz, C6H5CH2ONHCOCH═CHcis), 4.93 ppm (bs, 2H, C6H5CH2ONHCOCH═CH2).

1. additionwas slowly added over a period of 1 hour to the cooled solution
2. customNext, the ice bath was removed
3. waitthe reaction mixture was left
4. temperaturewarmed up gradually to room temperature
5. additionWater (250 mL) was added to the reaction
6. customthe layers were separated
7. washThe organic solution was washed with diluted hydrochloric acid (0.2N; 3×300 mL)
8. dry with materialThe organic layer was then dried over magnesium sulfate
9. filtrationfiltered
10. customthe solvent removed under reduced pressure
11. customThe residue was purified by flash chromatography
12. additiona mixture of hexane and ethyl acetate (70:30)
13. washto elute the product
14. customThe purification

ORD record

ord-ccab769d879543f4b0753a82c204404d

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07238339B2