Реакция #5355

Уравнение реакции

tetronic acid

triethylamine

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

10-(4-chlorophenyl)dec-9-enoic acid

HCl

→

4-hydroxy-3-[10-(4-chlorophenyl)-1-oxodec-9-enyl] -2(5H)-furanone

Выход 58.3%

Растворители

dimethylformamide

Условия реакции

Обработка

1. 1
   workup.ADDITIONare added
2. 2
   Экстракцияextracted three times with ethyl acetate
3. 3
   ПромывкаThe combined organic layers are washed with brine
4. 4
   Сушкаdried over Na2SO4
5. 5
   Концентрированиеconcentrated in vacuo
6. 6
   ДругоеThe residue is purified via flash chromatography on a 40 mm×150 mm silica gel column
7. 7
   Промывкаeluting with 5% methanol/ethyl acetate

Методика

To a stirring solution of 189 mg (1.89 mmol) of tetronic acid in 15 mL of dimethylformamide is added 290 μL (2.08 mmol) of triethylamine and 8 mg (66 μmol) of 4-dimethylaminopyridine at 0° C. Next, 427 mg (2.22 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 690 mg (2.20 mmol) of 10-(4-chlorophenyl)dec-9-enoic acid as a mixture of E and Z isomers 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 Na2SO4, and concentrated in vacuo. The residue is purified via flash chromatography on a 40 mm×150 mm silica gel column eluting with 5% methanol/ethyl acetate to give 400 mg (58%) of pure 4-hydroxy-3-[10-(4-chlorophenyl)-1-oxodec-9-enyl] -2(5H)-furanone as a mixture of E and Z isomers.

Источник