반응 #5345

반응 방정식

HCl

tetronic acid

triethylamine

stearoyl chloride

→

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

수율 58.0%

용매

methylene chloride

ethyl acetate

반응 조건

후처리

1. 1
   추출extracted with two 100 mL portions of methylene chloride
2. 2
   건조The combined organic layers are dried over MgSO4
3. 3
   농축concentrated in vacuo
4. 4
   기타affording crude compound

실험 절차

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.

출처