反応 #65973

反応方程式

phenol

2-Chloromethylquinoline

18-crown-6

hexane

potassium carbonate

→

pure title compound

収率 84.8%

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

収率 84.8%

溶媒

dichloromethane methanol

acetonitrile

反応条件

後処理

1. 1
   workup.ADDITIONis added in one portion
2. 2
   その他the mixture is placed in an oil bath
3. 3
   その他The solvent is removed in vacuo
4. 4
   その他the residue is partitioned between ethyl acetate and water
5. 5
   洗浄The organic phase is washed with brine
6. 6
   乾燥dried (MgSO4)
7. 7
   その他evaporated
8. 8
   その他to yield an oil which
9. 9
   その他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)

実験手順

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%).

出典