反応 #65991

反応方程式

2-(Chloromethyl)quinoline

2-methyl-5-hydroxy-1H-indene-3-acetic acid methyl ester

potassium carbonate

18-crown-6

→

desired product

収率 79.3%

2-Methyl-5-(2-quinolinylmethoxy)-1H-indene-3-acetic acid methyl ester

収率 79.3%

溶媒

acetonitrile

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture is stirred for 15 hours at 65° C
2. 2
   その他After the solvent is removed
3. 3
   その他the residue is partitioned between water and ethyl acetate
4. 4
   乾燥The organic phase is dried over MgSO4
5. 5
   その他evaporated
6. 6
   その他The crude product is purified by flash chromatography (eluant: methylene chloride-ethyl acetate)

実験手順

A mixture of 2-methyl-5-hydroxy-1H-indene-3-acetic acid methyl ester (1.8 g, 8.25 mmol), powdered anhydrous potassium carbonate (1.13 g, 8.25 mmol) and 18-crown-6 (0.219 g) in acetonitrile (21 mL) is stirred at room temperature for 15 minutes. 2-(Chloromethyl)quinoline (1.6 g, 9.08 mmol) is then added and the mixture is stirred for 15 hours at 65° C. After the solvent is removed, the residue is partitioned between water and ethyl acetate. The organic phase is dried over MgSO4 and evaporated. The crude product is purified by flash chromatography (eluant: methylene chloride-ethyl acetate) to afford 2.35 g (79%) of the desired product.

出典