反応 #1375830

反応方程式

DBU

KOH

2-acetoacetoxyethyl methacrylate

p-toluenesulfonyl azide

DBU

→

2-diazo-3-oxobutyroxyethyl methacrylate

収率 91.4%

溶媒

diethyl ether

dichloromethane

反応条件

後処理

1. 1
   その他2-Diazo-3-oxobutyroxyethyl methacrylate monomer was prepared
2. 2
   その他The organic layer was separated
3. 3
   抽出the aqueous layer was re-extracted with diethyl ether (50 ml)
4. 4
   洗浄washed sequentially with 3N HCl (50 ml), deionized water (2×50 ml) and saturated aqueous sodium chloride solution (50 ml)
5. 5
   その他The organic layer was dried
6. 6
   ろ過filtered
7. 7
   濃縮concentrated

実験手順

2-Diazo-3-oxobutyroxyethyl methacrylate monomer was prepared as follows: a mixture of 2-acetoacetoxyethyl methacrylate (4.28 gm, 20 mmol, available from Eastman Chemical, Kingsport, Tenn.), dichloromethane (30 ml), and p-toluenesulfonyl azide (3.94 gm, 20 mmol) was cooled to 0° C. and then DBU (1,8-diazabicyclo[5.4.0]undec-7-ene, 4.48 ml, 30 mmol) was added dropwise. After the addition of DBU, the reaction mixture was stirred at room temperature for 15 minutes and then poured into a mixture of 10% KOH (100 ml) and diethyl ether (50 ml). The organic layer was separated and the aqueous layer was re-extracted with diethyl ether (50 ml). The organic extracts were combined and then washed sequentially with 3N HCl (50 ml), deionized water (2×50 ml) and saturated aqueous sodium chloride solution (50 ml). The organic layer was dried using anhydrous magnesium sulfate, filtered, and concentrated to give 4.39 gm of 2-diazo-3-oxobutyroxyethyl methacrylate as a pale yellow oil. 1H NMR (400 MHz, CDCl3): δ 1.94 (s, 3H); 2.47 (s, 3H); 4.35-4.55 (m, 4H); 5.60 (s, 1H); 6.12 (s, 1H). IR: 2181 cm-1. Peak decomposition temperature: 156° C. (by DSC).

出典