반응 #84811

반응 방정식

3,5-dimethoxy-4-methylphenyl trifluoromethanesulfonate

2-furylboronic acid

LiCl

Na2CO3

→

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

수율 77.0%

용매

DME

반응 조건

후처리

1. 1
   기타the mixture was degassed
2. 2
   온도After cooling to room temperature
3. 3
   workup.ADDITIONthe reaction was diluted with H2O
4. 4
   추출extracted with EtOAc
5. 5
   세척The combined organics were washed with H2O, saturated aqueous NH4Cl, H2O and brine
6. 6
   건조dried over Na2SO4
7. 7
   농축concentrated in vacuo
8. 8
   기타Purification by chromatography (0-25% Et2O-hexanes)

실험 절차

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).

출처