反応 #5361

反応方程式

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

収率 24.0%

反応条件

後処理

1. 1
   抽出extracted three times with ether
2. 2
   乾燥The combined organic layers are dried over Na2SO4
3. 3
   濃縮concentrated in vacuo
4. 4
   その他giving a yellow solid
5. 5
   その他The residue is recrystallized from ethyl acetate/hexane at -78° C.

実験手順

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.

出典