反応 #1379898

反応方程式

O-benzyl hydroxylamine hydrochloride

N,N-diisopropylethylamine

acryloyl chloride

→

N-benzyloxyacrylarnide

収率 48.4%

N-benzyloxyacrylamide

収率 48.4%

溶媒

dichloromethane

dichloromethane

反応条件

後処理

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

実験手順

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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