反应 #71352

反应方程式

hydride

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

→

title compound

收率 49.8%

5-Nitro-pyridine-2-carbaldehyde

收率 49.8%

溶剂

DCM

反应条件

后处理

1. 1
   其他quenched by addition of an aqueous solution of potassium sodium tartrate
2. 2
   workup.ADDITIONdiluted with DCM and H2O
3. 3
   过滤filtered through a pad of celite
4. 4
   萃取The filtrate was extracted several times with DCM
5. 5
   洗涤The organic phase was washed with H2O and brine
6. 6
   干燥dried (Na2SO4)
7. 7
   过滤filtered
8. 8
   浓缩concentrated
9. 9
   其他The residue was purified by by silica gel column chromatography (EtOAc/Hex, 1:1)

实验过程

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]−.

来源