تفاعل #160170

معادلة التفاعل

(4-Ethoxycarbonylphenyl)-iodo-zinc

cyclopropanecarbonyl chloride

→

ethyl 4-(cyclopropanecarbonyl)benzoate

المردود 78.4%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGstirred for 2 hours
2. 2
   أخرىThe reaction mixture was quenched with 1M HCl (20 mL)
3. 3
   استخلاصextracted with ethyl acetate (2×50 mL)
4. 4
   غسيلThe organic layer was washed sequentially with sat. aq. NaHCO3 (5 mL) and brine solution (50 mL)
5. 5
   تجفيفdried over MgSO4
6. 6
   أخرىpurified by silica gel column chromatography

الإجراء التجريبي

(4-Ethoxycarbonylphenyl)-iodo-zinc (20 mL of 0.5 M in THF, 10.0 mmol) was added over 10 min to dichloro-bis(triphenylphosphoranyl)palladium (211 mg, 0.3 mmol) in THF (20 mL) under an atmosphere of nitrogen at 0° C. The reaction mixture was stirred for 15 minutes, cyclopropanecarbonyl chloride (941 mg, 817 μL, 9.0 mmol) was added dropwise at 0° C. and stirred for 2 hours. The reaction mixture was quenched with 1M HCl (20 mL), extracted with ethyl acetate (2×50 mL). The organic layer was washed sequentially with sat. aq. NaHCO3 (5 mL) and brine solution (50 mL), dried over MgSO4 and purified by silica gel column chromatography using 0-30% EtOAc/hexanes as eluent to give ethyl 4-(cyclopropanecarbonyl)benzoate (1.54 g, 71%) as a pale yellow oil. ESI-MS m/z calc. 218.0. Found 219.3 (M+1)+; Retention time: 1.57 minutes (3 min run).

المصدر