反应 #5344

反应方程式

tetronic acid

triethylamine

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

stearolic acid

HCl

→

4-hydroxy-3-(1-oxo-9-octadecynyl)-2(5H)-furanone

收率 56.0%

溶剂

methanol ethyl acetate

dimethylformamide

反应条件

后处理

1. 1
   萃取extracted with three 50 mL portions of ether
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 1.62 g (17.86 mmol) of tetronic acid in 50 mL of dimethylformamide is added 2.5 mL (17.86 mmol) of triethylamine and 652 mg of 4-dimethylaminopyridine at 0° C. Next, 3.71 g (19.35 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 5.0 g (17.86 mmol) of stearolic acid are added and the reaction is stirred overnight at room temperature. The reaction is acidified with 1.0N HCl and extracted with three 50 mL portions of ether. The combined organic layers are dried over MgSO4 and concentrated in vacuo affording crude compound. Pure material was obtained by flash chromatography with 10% methanol/ethyl acetate as eluant affording 3.3 g (56%) of 4-hydroxy-3-(1-oxo-9-octadecynyl)-2(5H)-furanone.

来源