Hydrochloric Acid → HCID 18996929, compound

HRID 374415Notes

Reaction equation

[CH:1]1([C:4]([CH3:6])=[O:5])[CH2:3][CH2:2]1.[H-].[Na+].[Cl:9][C:10]1[C:11]([C:17](OCC)=[O:18])=[N:12][CH:13]=[C:14]([Cl:16])[CH:15]=1.Cl>C(OCC)C>[CH:1]1([C:4](=[O:5])[CH2:6][C:17]([C:11]2[C:10]([Cl:9])=[CH:15][C:14]([Cl:16])=[CH:13][N:12]=2)=[O:18])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

Methyl cyclopropyl ketone (1.65 g) was added to a stirred suspension of sodium hydride (80% dispersion in oil; 0.6 g) in dry diethyl ether at 0° C. under an inert atmosphere. The mixture was stirred at 0° C. for one hour. Ethyl 3,5-dichloropyridine-2-carboxylate (2.16 g) was added and the mixture was stirred at 0° C. for 1 hour and then at room temperature overnight. Hydrochloric acid (2N) was added and the mixture was extracted with diethyl ether. The organic extracts were washed with water, dried (anthydrous magnesium sulphate), filtered and evaporated to give a brown gum which was purified by column chromatography on silica eluted with a mixture of ethyl acetate and hexane to yield 3-cyclopropyl-1-(3,5-dichloropyridin-2-yl)propan1,3-dione (1.35 g) as a colourless solid, m.p. 50.2°-52.7° C.

Workup

stirringthe mixture was stirred at 0° C. for 1 hour
customat room temperature
customovernight
extractionthe mixture was extracted with diethyl ether
washThe organic extracts were washed with water
dry with materialdried (anthydrous magnesium sulphate)
filtrationfiltered
customevaporated
customto give a brown gum which
customwas purified by column chromatography on silica
washeluted with a mixture of ethyl acetate and hexane

Sources & evidence

ORD record: ord-6cabe62e92064409b3c8f44025acba1a
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05480857

Reaction notes

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