반응 #1379898

반응 방정식

O-benzyl hydroxylamine hydrochloride

N,N-diisopropylethylamine

acryloyl chloride

→

N-benzyloxyacrylarnide

수율 48.4%

N-benzyloxyacrylamide

수율 48.4%

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   workup.ADDITIONwas slowly added over a period of 1 hour to the cooled solution
2. 2
   기타Next, the ice bath was removed
3. 3
   workup.WAITthe reaction mixture was left
4. 4
   온도warmed up gradually to room temperature
5. 5
   workup.ADDITIONWater (250 mL) was added to the reaction
6. 6
   기타the layers were separated
7. 7
   세척The organic solution was washed with diluted hydrochloric acid (0.2N; 3×300 mL)
8. 8
   건조The organic layer was then dried over magnesium sulfate
9. 9
   여과filtered
10. 10
    기타the solvent removed under reduced pressure
11. 11
    기타The residue was purified by flash chromatography
12. 12
    workup.ADDITIONa mixture of hexane and ethyl acetate (70:30)
13. 13
    세척to elute the product
14. 14
    기타The purification

실험 절차

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).

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