Reacción #84811

Ecuación de reacción

3,5-dimethoxy-4-methylphenyl trifluoromethanesulfonate

2-furylboronic acid

LiCl

Na2CO3

→

2-(3,5-dimethoxy-4-methylphenyl)furan

Rendimiento 77.0%

Disolventes

DME

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe mixture was degassed
2. 2
   TemperaturaAfter cooling to room temperature
3. 3
   workup.ADDITIONthe reaction was diluted with H2O
4. 4
   Extracciónextracted with EtOAc
5. 5
   LavadoThe combined organics were washed with H2O, saturated aqueous NH4Cl, H2O and brine
6. 6
   Secadodried over Na2SO4
7. 7
   Concentraciónconcentrated in vacuo
8. 8
   OtroPurification by chromatography (0-25% Et2O-hexanes)

Procedimiento

To a solution of 3,5-dimethoxy-4-methylphenyl trifluoromethanesulfonate (0.50 g, 1.67 mmol) in DME (15 mL) was added 2-furylboronic acid (0.245 g, 2.2 mmol), LiCl (0.149 g, 3.5 mmol), 2 M aqueous Na2CO3 (1.8 mL, 3.6 mmol) and tetrakis(triphenylphosphine)palladium (0.098 g, 0.085 mmol) and the mixture was degassed as described previously. The reaction was heated at 80° C. under argon for 22 hrs. After cooling to room temperature, the reaction was diluted with H2O and extracted with EtOAc. The combined organics were washed with H2O, saturated aqueous NH4Cl, H2O and brine, dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (0-25% Et2O-hexanes) gave 2-(3,5-dimethoxy-4-methylphenyl)furan as a white solid (0.28 g, 77% yield).

Fuente