Reaktion #330989

Reaktionsgleichung

Water

2-methoxy-5-(4-methyltetrahydro-2H-pyran-4-yl)benzaldehyde

nitronium tetrafluoroborate

→

captioned compound

Ausbeute 92.0%

2-methoxy-5-(4-methyltetrahydro-2H-pyran-4-yl)-3-nitrobenzaldehyde

Ausbeute 92.0%

Lösungsmittel

ethyl acetate

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwhile raising the temperature to −10° C
2. 2
   WaschenThe organic layer was washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine
3. 3
   Trocknendried over anhydrous sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   SonstigeThe solvent was then evaporated under reduced pressure
6. 6
   Sonstigethe obtained residue was purified by column chromatography (silica gel, hexane/ethyl acetate=90/10-30/70)

Vorschrift

A solution of the crude product containing 2-methoxy-5-(4-methyltetrahydro-2H-pyran-4-yl)benzaldehyde (0.719 g) in ethyl acetate (10.0 mL) was cooled to −40° C., and nitronium tetrafluoroborate (0.597 g, 4.49 mmol) was added thereto. The resulting mixture was stirred for 2 hours while raising the temperature to −10° C. Water was added to the reaction solution and the resulting solution was diluted with ethyl acetate. The organic layer was washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate and filtered. The solvent was then evaporated under reduced pressure, and the obtained residue was purified by column chromatography (silica gel, hexane/ethyl acetate=90/10-30/70) to obtain 0.644 g of the captioned compound (92% yield in 2 steps).

Quelle