Water → 2-Propionylpyridine
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[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N+:5]=1[O-])[CH2:2][CH3:3].O.C([O-])([O-])=[O:13].[Na+].[Na+]>C(O)(=O)C.C(OC(=O)C)(=O)C>[CH2:2]([C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)=[O:13])[CH3:3][CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N+:5]=1[O-])[CH2:2][CH3:3].O.C([O-])([O-])=[O:13].[Na+].[Na+]>C(O)(=O)C.C(OC(=O)C)(=O)C>[CH2:2]([C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)=[O:13])[CH3:3]19 g of 2-propylpyridine-N-oxide were dissolved in 40 ml of glacial acetic acid/40 ml of acetic anhydride and stirred for 6 hours at 85° C. and 12 hours at ambient temperature. Excess anhydride was decomposed with H2O, the solution was neutralized with Na2CO3 and extracted with diethyl ether. After rotating in the ether phase, 12 g of 2-(1-acetoxypropyl)-pyridine remained. This product was dissolved in 120 ml of methanol (70%), mixed with 4 g of NaOH and refluxed for 6 hours. After rotating out the methanol mixing took place with water, extraction with diethyl ether and the organic phase was rotated in. 5.4 g of 2-(1-hydroxypropyl)-pyridine were left. 0.5 g of this substance was refluxed for 2 hours with 1 g of MnO2 and 30 ml of dichloromethane. After filtering off the MnO2, rotation in took place to dryness. 0.3 g of ethyl-2-pyridylketone was obtained.
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