反応 #5343

反応方程式

tetronic acid

triethylamine

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

palmitoleic acid

HCl

→

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

収率 36.0%

溶媒

methanol ethyl acetate

dimethylformamide

反応条件

後処理

1. 1
   抽出extracted with four 100 mL portions of ethyl acetate
2. 2
   乾燥The combined organic layers are dried over MgSO4
3. 3
   濃縮concentrated in vacuo
4. 4
   その他affording crude compound

実験手順

To a stirring solution of 1.07 g (10.72 mmol) of tetronic acid in 30 mL of dimethylformamide is added 1.64 mL (11.97 mmol) of triethylamine and 428 mg of 4-dimethylaminopyridine at 0° C. Next, 2.44 g (12.77 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 3.0 g (11.79 mmol) of palmitoleic acid are added and the reaction is stirred for 3 days at room temperature. The reaction is acidified with 1.0N HCl and extracted with four 100 mL portions of ethyl acetate. 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 1.3 g (36%) of 4-hydroxy-3-((Z)-1-oxo-9-hexadecenyl)-2(5H)-furanone.

出典