تفاعل #51870

معادلة التفاعل

dimethyl 4-ethenyl-1,3-benzenedicarboxylate

AIBN

thioacetic acid

→

colorless oil

المردود 27.0%

dimethyl 4-[2-(acetylthio)ethyl]-1,3-benzenedicarboxylate

المردود 27.0%

المذيبات

benzene

NaHCO3

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe mixture was refluxed for 5 hours
2. 2
   استخلاصextracted with EtOAc (15 mL)
3. 3
   تجفيفThe organic layer was dried over MgSO4
4. 4
   تركيزconcentrated
5. 5
   أخرىThe residual material was purified by silica gel chromatography (hexanes/EtOAc=10:1)

الإجراء التجريبي

To a degassed solution of dimethyl 4-ethenyl-1,3-benzenedicarboxylate (415 mg, 1.88 mmol) in benzene (6 mL) were added AIBN (33 mg, 0.21 mmol) and thioacetic acid (0.27 mL, 3.78 mmol), and the mixture was refluxed for 5 hours. The reaction mixture was diluted with aqueous NaHCO3 solution (15 mL) and extracted with EtOAc (15 mL). The organic layer was dried over MgSO4 and concentrated. The residual material was purified by silica gel chromatography (hexanes/EtOAc=10:1) to give 0.150 g of colorless oil (27% yield).

المصدر