反応 #5367

反応方程式

tetronic acid

triethylamine

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

palmitic acid

HCl

→

4-hydroxy-3-[1-oxohexadecyl]-2(5H)-furanone

収率 91.0%

溶媒

dimethylformamide

反応条件

後処理

1. 1
   抽出extracted three times with ethyl acetate
2. 2
   洗浄The combined organic layers are washed with brine
3. 3
   乾燥dried over MgSO4
4. 4
   濃縮concentrated in vacuo
5. 5
   その他The residue is recrystallized from pentane

実験手順

To a stirring solution of 650 mg (6.5 mmol) of tetronic acid in 20 mL of dimethylformamide is added 1.0 mL (7.17 mmol) of triethylamine and 230 mg (1.88 mmol) of 4-dimethylaminopyridine at 0° C. Next, 1.50 g (7.81 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 2.0 g (7.81 mmol) of palmitic 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 ethyl acetate. The combined organic layers are washed with brine, dried over MgSO4, and concentrated in vacuo. The residue is recrystallized from pentane to give 2.0 g (91%) of 4-hydroxy-3-[1-oxohexadecyl]-2(5H)-furanone, mp 81°-83° C.

出典