Reaktion #329050

Reaktionsgleichung

N-methoxy-N-methyl-6-(trifluoromethyl)nicotinamide

cyclopropylmagnesium bromide

→

Cyclopropyl(6-(trifluoromethyl)pyridin-3-yl)methanone

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat room temperature
2. 2
   Sonstigeovernight
3. 3
   SonstigeThe reaction was quenched with 1N HCl
4. 4
   Extraktionthe water layer was extracted with ethyl acetate
5. 5
   Trocknendried with MgSO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   Sonstigeto obtain a crude brown oil
9. 9
   SonstigeThe crude product was purified by silica gel column (0-60% ethyl acetate/hexane)
10. 10
    Sonstigeto obtain a pale yellow solid

Vorschrift

To a stirred solution of N-methoxy-N-methyl-6-(trifluoromethyl)nicotinamide (1.00 g, 4.27 mmol) in tetrahydrofuran (30 mL) at 0° C. was added 0.5 M of cyclopropylmagnesium bromide in tetrahydrofuran (20 mL, 0.01 mol) dropwise over 15 minutes. The mixture was stirred at 0° C. for 30 minutes then at room temperature overnight. The reaction was quenched with 1N HCl. Solvent was pumped off and the water layer was extracted with ethyl acetate. Organics were combined and dried with MgSO4, filtered and concentrated to obtain a crude brown oil. The crude product was purified by silica gel column (0-60% ethyl acetate/hexane) to obtain a pale yellow solid.

Quelle