تفاعل #420545

معادلة التفاعل

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

4-methoxyphenylboronic acid

KF

→

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

المذيبات

toluene water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled to room temperature
2. 2
   استخلاصextracted with EtOAc (2×50 mL)
3. 3
   غسيلwashed with saturated NaHCO3 (50 mL) and brine (50 mL)
4. 4
   تجفيفdried over Na2SO4
5. 5
   أخرىPurification through silica gel column with 10-30% EtOAc/hexanes

الإجراء التجريبي

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%.

المصدر