반응 #5361

반응 방정식

HCl

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

4-(chlorophenoxy]pentanoic acid

thiotetronic acid

triethylamine

dimethylformamide

→

4-hydroxy-3-[5-(4-chlorophenoxy)-1-oxopentyl]-2(5H)-thiophenone

수율 24.0%

반응 조건

후처리

1. 1
   추출extracted three times with ether
2. 2
   건조The combined organic layers are dried over Na2SO4
3. 3
   농축concentrated in vacuo
4. 4
   기타giving a yellow solid
5. 5
   기타The residue is recrystallized from ethyl acetate/hexane at -78° C.

실험 절차

To a stirring solution of 224 mg (1.89 mmol) of thiotetronic acid in 10 mL of dimethylformamide is added 290 μL (2.08 mmol) of triethylamine and 77 mg (631 μmol) of 4-dimethylaminopyridine at 0° C. Next, 440 mg (2.29 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 530 mg (2.32 mmol) of 5-[4-(chlorophenoxy]pentanoic acid are added and the reaction mixture is stirred overnight at room temperature. The reaction is acidified with 1.0N HCl and extracted three times with ether. The combined organic layers are dried over Na2SO4 and concentrated in vacuo giving a yellow solid. The residue is recrystallized from ethyl acetate/hexane at -78° C. to give 150 mg (24%) of 4-hydroxy-3-[5-(4-chlorophenoxy)-1-oxopentyl]-2(5H)-thiophenone.

출처