反応 #5345

反応方程式

HCl

tetronic acid

triethylamine

stearoyl chloride

→

4-hydroxy-3-(1-oxooctadecyl)-2(5H)-furanone

収率 58.0%

溶媒

methylene chloride

ethyl acetate

反応条件

後処理

1. 1
   抽出extracted with two 100 mL portions of methylene chloride
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 1.6 g (16 mmol) of tetronic acid in 75 mL of methylene chloride is added 2.5 mL (17.86 mmol) of triethylamine and 640 mg of 4-dimethylaminopyridine at 0° C. Next, 5.0 g (17.6 mmol) of stearoyl chloride is added and the reaction is stirred overnight at room temperature. The reaction is acidified with 1.0N HCl and extracted with two 100 mL portions of methylene chloride. The combined organic layers are dried over MgSO4 and concentrated in vacuo affording crude compound. Pure material was obtained by trituration with ethyl acetate as affording 3.3 g (58%) of 4-hydroxy-3-(1-oxooctadecyl)-2(5H)-furanone.

出典