反应 #5345

反应方程式

HCl

tetronic acid

triethylamine

stearoyl chloride

→

4-hydroxy-3-(1-oxooctadecyl)-2(5H)-furanone

收率 58.0%

溶剂

methylene chloride

ethyl acetate

反应条件

后处理

1. 1
   萃取extracted with two 100 mL portions of methylene chloride
2. 2
   干燥The combined organic layers are dried over MgSO4
3. 3
   浓缩concentrated in vacuo
4. 4
   其他affording crude compound

实验过程

To a stirring solution of 1.6 g (16 mmol) of tetronic acid in 75 mL of methylene chloride is added 2.5 mL (17.86 mmol) of triethylamine and 640 mg of 4-dimethylaminopyridine at 0° C. Next, 5.0 g (17.6 mmol) of stearoyl chloride is added and the reaction is stirred overnight at room temperature. The reaction is acidified with 1.0N HCl and extracted with two 100 mL portions of methylene chloride. The combined organic layers are dried over MgSO4 and concentrated in vacuo affording crude compound. Pure material was obtained by trituration with ethyl acetate as affording 3.3 g (58%) of 4-hydroxy-3-(1-oxooctadecyl)-2(5H)-furanone.

来源