Reacción #420545

Ecuación de reacción

2,2-dimethyl-5-oxo-2,5-dihydrofuran-3-yl trifluoromethanesulfonate

4-methoxyphenylboronic acid

KF

→

4-(4-methoxyphenyl)-5,5-dimethylfuran-2(5H)-one

Disolventes

toluene water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to room temperature
2. 2
   Extracciónextracted with EtOAc (2×50 mL)
3. 3
   Lavadowashed with saturated NaHCO3 (50 mL) and brine (50 mL)
4. 4
   Secadodried over Na2SO4
5. 5
   OtroPurification through silica gel column with 10-30% EtOAc/hexanes

Procedimiento

To a 1:1 mixture of toluene/water (20 mL), were added 2,2-dimethyl-5-oxo-2,5-dihydrofuran-3-yl trifluoromethanesulfonate (100 mg, 0.38 mmol), 4-methoxyphenylboronic acid (87 mg, 0.57 mmol), PdCl2(PPh3)2 (27 mg, 0.038 mmol), 2M KF aqueous solution (0.95 mL, 1.9 mmol), benzyltriethylammonium chloride (8.7 mg, 0.038 mmol). The mixture was heated at 50° C. under N2 for 30 minutes, cooled to room temperature and extracted with EtOAc (2×50 mL). The organic layers were combined, washed with saturated NaHCO3 (50 mL) and brine (50 mL), dried over Na2SO4. Purification through silica gel column with 10-30% EtOAc/hexanes led to the product as yellow solid. Yield: 33 mg, 40%.

Fuente