反应 #7241

反应方程式

sodium potassium tartrate

3-n-propoxypicolinic acid n-propyl ester

DIBAL-H

→

3-n-propoxypyridine-2-carboxaldehyde

收率 113.5%

溶剂

CH2Cl2

CH2Cl2

CH2Cl2

反应条件

后处理

1. 1
   workup.WAITat room temperature for 3 hrs
2. 2
   workup.STIRRINGstirred vigorously for 65 hrs
3. 3
   其他The phases were separated
4. 4
   萃取the aqueous phase extracted with CH2Cl2 (3×20 mL)
5. 5
   干燥The combined organic phases were dried (Na2SO4)
6. 6
   浓缩concentrated
7. 7
   其他to give a yellow oil
8. 8
   workup.STIRRINGThe mixture was stirred for 19 hrs
9. 9
   过滤then filtered through celite
10. 10
    浓缩The filtrate was concentrated

实验过程

To a stirred solution of 3-n-propoxypicolinic acid n-propyl ester (0.1209 g, 0.541 mmol) in dry CH2Cl2 (5 mL) at −78° C. was added DIBAL-H (1.0 M, 2.5 mL, 2.5 mmol). The mixture was stirred at −78° C. for 1 hr, then at room temperature for 3 hrs. The mixture was poured into saturated aqueous sodium potassium tartrate (15 mL), diluted with CH2Cl2 (15 mL) and stirred vigorously for 65 hrs. The phases were separated and the aqueous phase extracted with CH2Cl2 (3×20 mL). The combined organic phases were dried (Na2SO4) and concentrated to give a yellow oil. The yellow oil was dissolved in CH2Cl2 (5 mL) and treated with MnO2 (˜85%, 0.4549 g, 4.45 mmol). The mixture was stirred for 19 hrs then filtered through celite. The filtrate was concentrated to give 0.1014 g of 3-n-propoxypyridine-2-carboxaldehyde as an orange oil. 1H NMR (CDCl3) d 1.09 (t, 3H, J=7.4 Hz), 1.91 (sextet, 2H, J=7.1 Hz), 4.07 (t, 2H, J=6.6 Hz), 7.38–7.47 (m, 2H), 8.39 (dd, 2H, J=4.4, 1.4 Hz), 10.43 (s, 1H).

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