反応 #347806

反応方程式

1-Chloroethyl 4-acryloyloxybutyl carbonate

potassium acrylate

→

title product

収率 89.4%

1-Acryloyloxyethyl 4-Acryloyloxybutyl Carbonate

収率 89.4%

溶媒

dimethylformamide

反応条件

後処理

1. 1
   その他as described in Preparation 10
2. 2
   その他After 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
   その他After separating the phases the aqueous layer
6. 6
   抽出is extracted with dichloromethane (3×30 ml)
7. 7
   洗浄the combined organic phase washed with saturated aqueous sodium hydrogen carbonate (50 ml)
8. 8
   乾燥The organic phase is dried (MgSO4)
9. 9
   その他the solvent removed under reduced pressure

実験手順

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).

出典