Reacción #54074

Ecuación de reacción

3-thiopheneboronic acid

trifluoromethanesulfonic acid 2,2,4-trimethyl-1,2-dihydroquinolin-6-yl ester

KF

→

2,2,4-trimethyl-6-thiophen-3-yl-1,2-dihydroquinoline

Rendimiento 32.1%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe flask was evacuated
2. 2
   Otroflushed three times with argon
3. 3
   FiltraciónThe reaction mixture was filtered through diatomaceous earth
4. 4
   workup.ADDITIONdiluted with EtOAc (50 mL)
5. 5
   LavadoThe mixture was sequentially washed with water (10 mL), NaOH (1.0 M, 10 mL), and brine (10 mL)
6. 6
   SecadoThe organic phase was dried over sodium sulfate (Na2SO4)
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated in vacuo
9. 9
   OtroThe crude residue was purified by chromatography (silica gel, 30% dichloromethane in hexanes)

Procedimiento

To a dry 50 mL round bottom flask charged with a mixture of trifluoromethanesulfonic acid 2,2,4-trimethyl-1,2-dihydroquinolin-6-yl ester (0.50 g, 1.56 mmol), Pd(OAc)2 (0.035 g, 0.156 mmol), di-tert-butylbiphenylphosphine (DTBBPP) (0.093 g, 0.312 mmol), and KF (0.27 g, 4.67 mmol) suspended in THF (5 mL), was added 3-thiopheneboronic acid (0.30 g, 2.33 mmol). The flask was evacuated and flushed three times with argon and the reaction mixture was allowed to stir at room temperature for 2 days. The reaction mixture was filtered through diatomaceous earth and diluted with EtOAc (50 mL). The mixture was sequentially washed with water (10 mL), NaOH (1.0 M, 10 mL), and brine (10 mL). The organic phase was dried over sodium sulfate (Na2SO4), filtered, and concentrated in vacuo. The crude residue was purified by chromatography (silica gel, 30% dichloromethane in hexanes) to give 2,2,4-trimethyl-6-thiophen-3-yl-1,2-dihydroquinoline (0.128 g, 32%).

Fuente