Reaktion #71352

Reaktionsgleichung

hydride

5-nitro-pyridine-2-carboxylic acid ethyl ester

→

title compound

Ausbeute 49.8%

5-Nitro-pyridine-2-carbaldehyde

Ausbeute 49.8%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigequenched by addition of an aqueous solution of potassium sodium tartrate
2. 2
   workup.ADDITIONdiluted with DCM and H2O
3. 3
   Filtrationfiltered through a pad of celite
4. 4
   ExtraktionThe filtrate was extracted several times with DCM
5. 5
   WaschenThe organic phase was washed with H2O and brine
6. 6
   Trocknendried (Na2SO4)
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated
9. 9
   SonstigeThe residue was purified by by silica gel column chromatography (EtOAc/Hex, 1:1)

Vorschrift

Diisobutylaluminiumo hydride (1 M in DCM, 44 mL, 44 mmol, 1.3 equiv) was added dropwise to a cold (−78° C.) solution of 5-nitro-pyridine-2-carboxylic acid ethyl ester (step 39.4) (6.56 g, 33.5 mmol) in DCM (130 mL), under an argon atmosphere. The reaction mixture was allowed to warm to 5° C., quenched by addition of an aqueous solution of potassium sodium tartrate, diluted with DCM and H2O, stirred for 16 h at rt, and filtered through a pad of celite. The filtrate was extracted several times with DCM. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by by silica gel column chromatography (EtOAc/Hex, 1:1) to provide 2.54 g of the title compound as a beige solid: ESI-MS: 151.1 [M−H]−.

Quelle