반응 #5355

반응 방정식

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

수율 58.3%

용매

dimethylformamide

반응 조건

후처리

1. 1
   workup.ADDITIONare added
2. 2
   추출extracted three times with ethyl acetate
3. 3
   세척The combined organic layers are washed with brine
4. 4
   건조dried over Na2SO4
5. 5
   농축concentrated in vacuo
6. 6
   기타The residue is purified via flash chromatography on a 40 mm×150 mm silica gel column
7. 7
   세척eluting with 5% methanol/ethyl acetate

실험 절차

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.

출처