반응 #65973

반응 방정식

phenol

2-Chloromethylquinoline

18-crown-6

hexane

potassium carbonate

→

pure title compound

수율 84.8%

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

수율 84.8%

용매

dichloromethane methanol

acetonitrile

반응 조건

후처리

1. 1
   workup.ADDITIONis added in one portion
2. 2
   기타the mixture is placed in an oil bath
3. 3
   기타The solvent is removed in vacuo
4. 4
   기타the residue is partitioned between ethyl acetate and water
5. 5
   세척The organic phase is washed with brine
6. 6
   건조dried (MgSO4)
7. 7
   기타evaporated
8. 8
   기타to yield an oil which
9. 9
   기타The 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)

실험 절차

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%).

출처