Reaktion #464746

Reaktionsgleichung

Methylmagnesium bromide

N-(3,5-dichlorophenyl)-2-(6-formyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide

ammonium chloride

ethyl acetate

→

N-(3,5-dichlorophenyl)-2[2,3-dihydro-6-(1-hydroxyethyl)-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl]-2-methylpropanamide

Lösungsmittel

ether

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe organic phase was washed (brine)
2. 2
   Trocknendried (magnesium sulphate)
3. 3
   Sonstigeevaporated
4. 4
   SonstigeThe residue was purified
5. 5
   Sonstigeby dry column chromatography on silica gel
6. 6
   Wascheneluting with dichloromethane/ethyl acetate

Vorschrift

Methylmagnesium bromide (1.7 ml of a 3M solution in ether) was added dropwise to a stirred solution of N-(3,5-dichlorophenyl)-2-(6-formyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide (1.0 g) in dry tetrahydrofuran under an inert atmosphere at -5° C. After 1 hour at that temperature, ammonium chloride solution (saturated) and ethyl acetate were added. The organic phase was washed (brine), dried (magnesium sulphate) and evaporated. The residue was purified by dry column chromatography on silica gel, eluting with dichloromethane/ethyl acetate to give N-(3,5-dichlorophenyl)-2[2,3-dihydro-6-(1-hydroxyethyl)-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl]-2-methylpropanamide (compound 123, 0.27 g) as a cream solid, m.p. 85-88° C.

Quelle