反应 #82205

反应方程式

isobutyramide

1,3-dichloroacetone

NaHCO3

MgSO4

→

desired product

收率 46.0%

4-Chloromethyl-4-hydroxy-2-isopropyloxazoline

收率 46.0%

溶剂

acetone

反应条件

后处理

1. 1
   温度The mixture was heated
2. 2
   温度at reflux under argon for 63 hrs
3. 3
   过滤vacuum filtered
4. 4
   浓缩concentrated in vacuo to a dark brown semi-solid
5. 5
   其他The residue was purified by SiO2 flash chromatography

实验过程

To a solution of isobutyramide (9.876 g, 0.1122 mol) in acetone (130 mL) was added 1,3-dichloroacetone (10.0 g, 0.0748 mol), NaHCO3 (9.429 g, 0.1122 mol), and MgSO4 (18.01 g, 0.1496 mol). The mixture was heated at reflux under argon for 63 hrs, then cooled to room temperature, vacuum filtered, and concentrated in vacuo to a dark brown semi-solid. The residue was purified by SiO2 flash chromatography using a gradient of EtOAc/CH2Cl2 (5%, 10%, 20%, 40%) to obtain the desired product as an orange liquid (6.06 g, 0.0341 mol, 46%): 1H NMR (CDCl3) δ 1.20-1.28 (m, 6H), 2.56-2.72 (m, 1H), 3.70 (s, 2H), 4.18 (d, J=9.6 Hz, 1H), 4.38 (d, J=9.6 Hz, 1H). Mass spectrum: (M+H)+ =178, 180.

来源