반응 #347806

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1-Chloroethyl 4-acryloyloxybutyl carbonate

potassium acrylate

→

title product

수율 89.4%

1-Acryloyloxyethyl 4-Acryloyloxybutyl Carbonate

수율 89.4%

용매

dimethylformamide

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후처리

1. 1
   기타as described in Preparation 10
2. 2
   기타After 5 days at 20° C. the solvent is removed under reduced pressure
3. 3
   workup.DISSOLUTIONthe residue dissolved
4. 4
   workup.ADDITIONby adding dichloromethane (60 ml) and water (30 ml)
5. 5
   기타After separating the phases the aqueous layer
6. 6
   추출is extracted with dichloromethane (3×30 ml)
7. 7
   세척the combined organic phase washed with saturated aqueous sodium hydrogen carbonate (50 ml)
8. 8
   건조The organic phase is dried (MgSO4)
9. 9
   기타the solvent removed under reduced pressure

실험 절차

1-Chloroethyl 4-acryloyloxybutyl carbonate (1.253 g, 5.00 mmol) prepared as described in Preparation 10 is added to a suspension of freeze dried potassium acrylate (0.606 g, 5.50 mmol) and 18-crown-6 (0.066 g, 0.25 mmol) in dimethylformamide (50 ml) under a dry N2 atmosphere. After 5 days at 20° C. the solvent is removed under reduced pressure and the residue dissolved by adding dichloromethane (60 ml) and water (30 ml). After separating the phases the aqueous layer is extracted with dichloromethane (3×30 ml) and the combined organic phase washed with saturated aqueous sodium hydrogen carbonate (50 ml). The organic phase is dried (MgSO4) and the solvent removed under reduced pressure to give 1.28 g (89%) of the title product. 1H NMR (60 MHz, CDCl3): δ 1.58 (3 H, d, J=5 Hz, CH3 --CH), 1.80 (4 H, m, CH2 --CH2), 4.24 (4 H, m, 2×CH2 --O), 5.7-6.7 (6 H, m, 2×CH=CH2), 6.87 (1 H, k, J=5 Hz, CH--CH3).

출처