تفاعل #5361

معادلة التفاعل

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

المردود 24.0%

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted three times with ether
2. 2
   تجفيفThe combined organic layers are dried over Na2SO4
3. 3
   تركيزconcentrated in vacuo
4. 4
   أخرىgiving a yellow solid
5. 5
   أخرىThe residue is recrystallized from ethyl acetate/hexane at -78° C.

الإجراء التجريبي

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.

المصدر