반응 #8320

반응 방정식

hydrochloric acid

3-chloro-4-fluorophenylacetonitrile

6-methyl-pyridine-2-carboxylic acid methyl ester

sodium hydride

→

title compound

2-(3-Chloro-4-fluoro-phenyl)-1-(6-methyl-pyridin-2-yl)-ethanone

용매

ethanol

반응 조건

후처리

1. 1
   온도The mixture is refluxed for 2.5 h
2. 2
   농축The mixture is concentrated in vacuo
3. 3
   workup.ADDITIONConcentrated hydrochloric acid (50 mL) is added to the mixture after which it
4. 4
   온도is refluxed for 1.5 h
5. 5
   workup.ADDITIONThe mixture is poured over ice
6. 6
   추출The mixture is extracted with methylene chloride
7. 7
   건조the organic portions dried over anhydrous sodium sulfate
8. 8
   여과The mixture is filtered
9. 9
   농축concentrated in vacuo

실험 절차

A dispersion of sodium hydride, (60% in mineral oil, 0.7 g, 17.7 mmol) is added to ethanol (25 mL). When gas evolution ceases, 3-chloro-4-fluorophenylacetonitrile (Fluorochemicals, 2.0 g, 11.8 mmol) and 6-methyl-pyridine-2-carboxylic acid methyl ester (1.8 g, 11.8 mmol), are added. The mixture is refluxed for 2.5 h and adjusted to pH 7 with 1 N hydrochloric acid. The mixture is concentrated in vacuo. Concentrated hydrochloric acid (50 mL) is added to the mixture after which it is refluxed for 1.5 h. The mixture is poured over ice and adjusted to pH 8 with 5 N sodium hydroxide. The mixture is extracted with methylene chloride and the organic portions dried over anhydrous sodium sulfate. The mixture is filtered and concentrated in vacuo to yield the title compound, 2.1 g (68%), as a yellowish solid.

출처