Reaktion #603766

Reaktionsgleichung

methyl 4-amino-3-chloro-6-(3-fluoro-4-formylphenyl)-5-methylpicolinate

potassium carbonate

dimethyl(1-diazo-2-oxopropyl)phosphonate

→

title compound

Ausbeute 69.9%

methyl 4-amino-3-chloro-6-(4-ethynyl-3-fluorophenyl)-5-methylpicolinate

Ausbeute 69.9%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched with saturated aqueous sodium bicarbonate
2. 2
   Extraktionextracted with ethyl acetate (3×)
3. 3
   Filtrationfiltered
4. 4
   SonstigePurification by flash chromatography (0-50% ethyl acetate/hexanes)

Vorschrift

To a solution of methyl 4-amino-3-chloro-6-(3-fluoro-4-formylphenyl)-5-methylpicolinate (358 mg, 1.1 mmol) and potassium carbonate (537 mg, 3.9 mmol) in methanol (11 mL) at room temperature was added 1 mL of dimethyl(1-diazo-2-oxopropyl)phosphonate (Bestmann-Ohira reagent, crude reagent) for 3 h. The reaction was quenched with saturated aqueous sodium bicarbonate and extracted with ethyl acetate (3×). The combined organic layers were dried organics over anhydrous sodium sulfate, filtered, and adsorbed onto silica gel. Purification by flash chromatography (0-50% ethyl acetate/hexanes) provided the title compound as a yellow solid (245 mg, 69%).

Quelle