Reacción #1701365

Ecuación de reacción

1,1-dimethoxy-3-(2,4-dichlorophenyl)propan-2-one

3-pyridyllithium

n-butyllithium

3-bromopyridine

→

1,1-dimethoxy-2-hydroxy-2-(3-pyridyl)-3-(2,4-dichlorophenyl)-propane

Disolventes

Et2O

water

Isopropanol

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAt -70° C.
2. 2
   workup.WAITAfter half an hour at -70° C.
3. 3
   Extracciónthe reaction solution is extracted with 1N hydrochloric acid
4. 4
   Extracciónextracted with methylene chloride (CH2Cl2)
5. 5
   SecadoAfter drying over Na2SO4, all the volatile constituents
6. 6
   Otroare removed in a rotary evaporator
7. 7
   OtroA yellowish red oil is obtained

Procedimiento

At -70° C., 88.9 g (0.337 mol) of 1,1-dimethoxy-3-(2,4-dichlorophenyl)propan-2-one in 100 ml of diethyl ether (Et2O) is dripped into a solution of 0.371 mol of 3-pyridyllithium in 1.1 liters of Et2O prepared from n-butyllithium and 3-bromopyridine. After half an hour at -70° C., the solution is slowly heated up to 0° C. Isopropanol and then water is added, and the reaction solution is extracted with 1N hydrochloric acid. The acidic aqueous phase is then neutralized with NaHCO3 and extracted with methylene chloride (CH2Cl2). After drying over Na2SO4, all the volatile constituents are removed in a rotary evaporator. A yellowish red oil is obtained. Yield: 56.1 g (48.7%).

Fuente