Reaktion #44630

Reaktionsgleichung

Lithium hydroxide monohydrate

tetrahydrofuran

[(4R,9aS)-6-oxo-4-(3,4,5-trifluorophenyl)octahydropyrido[2,1-c][1,4]oxazin-7-yl]phosphonic acid diethyl ester

3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde

→

title compound

Ausbeute 38.2%

(E)-(4R,9aS)-7-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]-4-(3,4,5-trifluorophenyl)hexahydropyrido[2,1-c][1,4]oxazin-6-one

Ausbeute 38.2%

Lösungsmittel

ethanol

water

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting reaction solution
2. 2
   SonstigeThe organic layer was separated
3. 3
   Waschenwashed with saturated saline
4. 4
   Trocknendried over magnesium sulfate
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigeThe residue was purified by silica gel column chromatography (carrier: Chromatorex NH, eluting solvent: heptane-ethyl acetate system)

Vorschrift

Lithium hydroxide monohydrate (63.4 mg) was added to a solution mixture of tetrahydrofuran (6 mL) and ethanol (2 mL) of [(4R,9aS)-6-oxo-4-(3,4,5-trifluorophenyl)octahydropyrido[2,1-c][1,4]oxazin-7-yl]phosphonic acid diethyl ester (372 mg) and 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (229 mg) at room temperature. The resulting reaction solution was stirred at room temperature for 2 hr, and ethyl acetate and water were added thereto. The organic layer was separated, washed with saturated saline, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH, eluting solvent: heptane-ethyl acetate system) to give 163.2 mg of the title compound. The physical property values of this compound were as follows:

Quelle