반응 #71352

반응 방정식

hydride

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

→

title compound

수율 49.8%

5-Nitro-pyridine-2-carbaldehyde

수율 49.8%

용매

DCM

반응 조건

후처리

1. 1
   기타quenched by addition of an aqueous solution of potassium sodium tartrate
2. 2
   workup.ADDITIONdiluted with DCM and H2O
3. 3
   여과filtered through a pad of celite
4. 4
   추출The filtrate was extracted several times with DCM
5. 5
   세척The organic phase was washed with H2O and brine
6. 6
   건조dried (Na2SO4)
7. 7
   여과filtered
8. 8
   농축concentrated
9. 9
   기타The residue was purified by by silica gel column chromatography (EtOAc/Hex, 1:1)

실험 절차

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]−.

출처