반응 #7241

반응 방정식

sodium potassium tartrate

3-n-propoxypicolinic acid n-propyl ester

DIBAL-H

→

3-n-propoxypyridine-2-carboxaldehyde

수율 113.5%

용매

CH2Cl2

CH2Cl2

CH2Cl2

반응 조건

후처리

1. 1
   workup.WAITat room temperature for 3 hrs
2. 2
   workup.STIRRINGstirred vigorously for 65 hrs
3. 3
   기타The phases were separated
4. 4
   추출the aqueous phase extracted with CH2Cl2 (3×20 mL)
5. 5
   건조The combined organic phases were dried (Na2SO4)
6. 6
   농축concentrated
7. 7
   기타to give a yellow oil
8. 8
   workup.STIRRINGThe mixture was stirred for 19 hrs
9. 9
   여과then filtered through celite
10. 10
    농축The filtrate was concentrated

실험 절차

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).

출처