반응 #92685

반응 방정식

methyl 5-hydroxy-6-nitronicotinate

(2-fluorophenyl)methanol

tributylphosphine

diethyl azodicarboxylate

→

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

용매

THF

ethyl acetate

water

반응 조건

후처리

1. 1
   온도cooling
2. 2
   기타a layer separation operation
3. 3
   세척The organic layer was washed with saturated brine
4. 4
   건조dried over anhydrous magnesium sulfate
5. 5
   기타the solvent was evaporated under reduced pressure
6. 6
   기타The obtained residue was purified by silica gel column chromatography

실험 절차

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.

출처