Reaction #5344

Reaction equation

tetronic acid

triethylamine

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

stearolic acid

HCl

→

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

Yield 56.0%

Solvents

methanol ethyl acetate

dimethylformamide

Conditions

Workup

1. 1
   Extractionextracted with three 50 mL portions of ether
2. 2
   DryingThe combined organic layers are dried over MgSO4
3. 3
   Concentrationconcentrated in vacuo
4. 4
   Otheraffording crude compound

Procedure

To a stirring solution of 1.62 g (17.86 mmol) of tetronic acid in 50 mL of dimethylformamide is added 2.5 mL (17.86 mmol) of triethylamine and 652 mg of 4-dimethylaminopyridine at 0° C. Next, 3.71 g (19.35 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 5.0 g (17.86 mmol) of stearolic acid are added and the reaction is stirred overnight at room temperature. The reaction is acidified with 1.0N HCl and extracted with three 50 mL portions of ether. 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 3.3 g (56%) of 4-hydroxy-3-(1-oxo-9-octadecynyl)-2(5H)-furanone.

Source