Reaktion #41779

Reaktionsgleichung

methyl-5-hydroxypyridine-3-carboxylate

Potassium bis(trimethylsilyl)amide

1-fluoro-4-nitrobenzene

Potassium carbonate

→

methyl-5-(4-nitrophenoxy)pyridine-3-carboxylate

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was then concentrated
2. 2
   Sonstigepartitioned between ethyl acetate and water
3. 3
   SonstigeThe organic layer was separated
4. 4
   Waschenwashed with brine
5. 5
   Sonstigedried
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuum
8. 8
   Sonstigeto give brown solid
9. 9
   SonstigePurification on silica gel methyl-5-(4-nitrophenoxy)pyridine-3-carboxylate

Vorschrift

The mixture containing methyl-5-hydroxypyridine-3-carboxylate (1 eq), Potassium bis(trimethylsilyl)amide (1.2 eq) was stirred in N,N-dimethylformamide for 2 hours at room temperature. To this mixture was added 1-fluoro-4-nitrobenzene (1.1 eq) and Potassium carbonate (1.2 eq) and stirred at 80° C. for 16 h. The reaction mixture was then concentrated and partitioned between ethyl acetate and water. The organic layer was separated and washed with brine, dried, filtered and concentrated in vacuum to give brown solid. Purification on silica gel methyl-5-(4-nitrophenoxy)pyridine-3-carboxylate. MS: MH+=274.

Quelle