Reaction #5345

Reaction equation

HCl

tetronic acid

triethylamine

stearoyl chloride

→

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

Yield 58.0%

Solvents

methylene chloride

ethyl acetate

Conditions

Workup

1. 1
   Extractionextracted with two 100 mL portions of methylene chloride
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 1.6 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.

Source