Reacción #1175086

Ecuación de reacción

2-(Chloromethyl)quinoline

6-hydroxy-α-methyl-2-naphthaleneacetic acid

sodium methoxide

→

oil

Rendimiento 151.1%

α-Methyl-6-(2-quinolinylmethoxy)-2-naphthaleneacetic acid

Rendimiento 151.1%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter 10 minutes the solvent is removed
2. 2
   OtroThe reaction mixture is partitioned between water and methylene chloride
3. 3
   Lavadothe organic layer is washed with water
4. 4
   Otroevaporated

Procedimiento

To a solution of 6-hydroxy-α-methyl-2-naphthaleneacetic acid (10.8 g, 50 mmol) in methanol (100 ml) is added sodium methoxide (100 mmol). After 10 minutes the solvent is removed and replaced with dimethylformamide (250 ml). 2-(Chloromethyl)quinoline (17.8 g, 100 mmol) is then added and the reaction mixture is stirred for 8 days at room temperature. The reaction mixture is partitioned between water and methylene chloride, the organic layer is washed with water and evaporated to yield 27 g of an oil. Recrystallization of this oil twice from acetonitrile gives 10.6 g of white crystals of intermediate ether ester (42% yield, m.p. 106°-108° C.).

Fuente