反応 #5359

反応方程式

thiotetronic acid

triethylamine

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

oleic acid

HCl

→

4-hydroxy-3-[(Z)-1-oxo-9-octadecenyl]-2(5H)-thiophenone

収率 33.0%

溶媒

dimethylformamide

反応条件

後処理

1. 1
   抽出extracted three times with diethyl ether
2. 2
   洗浄The combined organic layers are washed with brine
3. 3
   乾燥dried over Na2SO4
4. 4
   ろ過filtered
5. 5
   濃縮concentrated in vacuo
6. 6
   洗浄eluting with 100% ethyl acetate

実験手順

To a stirring solution of 1.71 g (14.75 mmol) of thiotetronic acid in 10 mL of dimethylformamide is added 2.22 mL (17.2 mmol) of triethylamine and 592 mg (4.85 mmol) of 4-diemthylaminopyridine at 0° C. Next, 3.38 g (17.6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 5.0 g (17.7 mmol) of oleic 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 diethyl ether. The combined organic layers are washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue is subjected to HPLC chromatography (2 inch Dynamax silica gel column, 25 mL/min) eluting with 100% ethyl acetate to give 1.85 g (33%) of 4-hydroxy-3-[(Z)-1-oxo-9-octadecenyl]-2(5H)-thiophenone as an oil.

出典