反応 #42155

反応方程式

4-dimethylaminobromobenzene

methyl methacrylate

dicyclohexylmethylamine

→

(E)-3-(4-dimethylaminophenyl)-2-methylacrylic acid methyl ester

収率 86.7%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   その他A 30-ml four-necked flask was equipped with a stirrer
2. 2
   workup.ADDITIONadded into the flask
3. 3
   その他The flask was purged with argon
4. 4
   workup.STIRRINGby stirring at 30° C. for 25 hours
5. 5
   その他After the completion of the reaction, 5 ml of toluene and 10 ml of saturated sodium chloride solution
6. 6
   workup.ADDITIONwere added
7. 7
   その他followed by separation
8. 8
   その他The organic phase was purified by column chromatography

実験手順

A 30-ml four-necked flask was equipped with a stirrer, a thermometer and a reflux condenser. 1.000 g (5 mmol) of 4-dimethylaminobromobenzene, 1.001 g (10 mmol) of methyl methacrylate, 0.011 g (0.012 mmol) of tris (dibenzylideneacetone)dipalladium (0), 1.074 g (5.5mmol) of dicyclohexylmethylamine and 5 ml of tetrahydrofuran were weighed in the flask, followed by stirring. Further, 0.026 g (0.05 mmol) of tri-tert-butylphosphonium tetraphenylborate obtained in Example A-1 was weighed in air and added into the flask. The flask was purged with argon, followed by stirring at 30° C. for 25 hours. After the completion of the reaction, 5 ml of toluene and 10 ml of saturated sodium chloride solution were added, followed by separation. The organic phase was purified by column chromatography to afford 0.951 g of (E)-3-(4-dimethylaminophenyl)-2-methylacrylic acid methyl ester (yield: 87 mol % based on 4-dimethylaminobromobenzene). The identification of the product was made by 1H-NMR and 13C-NMR.

出典