Reaktion #92685

Reaktionsgleichung

methyl 5-hydroxy-6-nitronicotinate

(2-fluorophenyl)methanol

tributylphosphine

diethyl azodicarboxylate

→

methyl 5-[(2-fluorobenzyl)oxy]-6-nitronicotinate

Lösungsmittel

THF

ethyl acetate

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   Sonstigea layer separation operation
3. 3
   WaschenThe organic layer was washed with saturated brine
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   Sonstigethe solvent was evaporated under reduced pressure
6. 6
   SonstigeThe obtained residue was purified by silica gel column chromatography

Vorschrift

To a solution of 2 g of methyl 5-hydroxy-6-nitronicotinate, 1.62 ml of (2-fluorophenyl)methanol, and 3.99 ml of tributylphosphine in 40 ml of THF was added 2.54 ml of diethyl azodicarboxylate under ice-cooling, followed by stirring for 1 hour under ice-cooling and at room temperature for 2 hours. To the reaction mixture were added water and ethyl acetate to carry out a layer separation operation. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 2.58 g of methyl 5-[(2-fluorobenzyl)oxy]-6-nitronicotinate.

Quelle