Reacción #65973

Ecuación de reacción

phenol

2-Chloromethylquinoline

18-crown-6

hexane

potassium carbonate

→

pure title compound

Rendimiento 84.8%

6-(2-quinolinylmethoxy)-2-methyl-1-indanone

Rendimiento 84.8%

Disolventes

dichloromethane methanol

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONis added in one portion
2. 2
   Otrothe mixture is placed in an oil bath
3. 3
   OtroThe solvent is removed in vacuo
4. 4
   Otrothe residue is partitioned between ethyl acetate and water
5. 5
   LavadoThe organic phase is washed with brine
6. 6
   Secadodried (MgSO4)
7. 7
   Otroevaporated
8. 8
   Otroto yield an oil which
9. 9
   OtroThe crude product is purified by flash chromatography (on silica Merck-60, absorbed in methylene chloride, eluted with CH2Cl2 -ethyl acetate 90:10 and 85:15)

Procedimiento

A mixture of the phenol (15. 1 6 g, 93.58 mmole) of Step D, powdered anhydrous potassium carbonate (12.93 g, 93.6 mmole), 18-crown-6 (2.47 g, 9.36 mmole) and dry acetonitrile (200 mL) is stirred at room temperature under a nitrogen for 15 minutes. 2-Chloromethylquinoline (free base, freshly prepared from 18.29 g or 102.96 mmole of the hydrochloride salt) is added in one portion and the mixture is placed in an oil bath heated at 65° C. for 11 hours (TLC, dichloromethane-methanol 9: 1, UV). The solvent is removed in vacuo and the residue is partitioned between ethyl acetate and water. The organic phase is washed with brine, dried (MgSO4) and evaporated to yield an oil which solidifies upon trituration with hexane (ca. 31 g). The crude product is purified by flash chromatography (on silica Merck-60, absorbed in methylene chloride, eluted with CH2Cl2 -ethyl acetate 90:10 and 85:15) to provide 5.95 g of slightly impure material together with 24.55 g of the pure title compound (pale yellow solid, 84.8%).

Fuente