Reaktion #2160902

Reaktionsgleichung

diethylamine

2-bromoacetonaphthone

→

title compound

2-(Diethylamino)-1-(naphthalen-1-yl)ethanone

Lösungsmittel

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeMonitor the progress of the reaction by thin-layer chromatography on silica gel (ethyl acetate:hexane, 1:1)
2. 2
   ExtraktionExtract the reaction mixture with 3×150 mL of 3N HCl
3. 3
   Extraktionthen extract with 3×150 mL of methylene chloride
4. 4
   Trocknendry over sodium sulfate
5. 5
   SonstigeRemove the solvent in vacuo, and chromatograph the resultant oil on 2200 g of silica gel
6. 6
   Wascheneluting initially with methylene chloride and later with ethyl acetate
7. 7
   workup.ADDITIONcontaining product
8. 8
   Sonstigeremove the solvent in vacuo

Vorschrift

To a solution of 38.1 g (0.52 mol) of diethylamine in 80 mL of toluene and cooled in an ice bath to 0° C. add dropwise a solution of 65.0 g (0.26 mol) of 2-bromoacetonaphthone in 300 mL of toluene. Stir the reaction mixture overnight. Monitor the progress of the reaction by thin-layer chromatography on silica gel (ethyl acetate:hexane, 1:1). Extract the reaction mixture with 3×150 mL of 3N HCl. Adjust the pH of the combined aqueous layers to pH=10 with 50% sodium hydroxide then extract with 3×150 mL of methylene chloride. Combine the extracts and dry over sodium sulfate. Remove the solvent in vacuo, and chromatograph the resultant oil on 2200 g of silica gel, eluting initially with methylene chloride and later with ethyl acetate. Combine the fractions containing product and remove the solvent in vacuo to obtain the title compound.

Quelle