[CH2:1]([C:5]1[C:6]([CH3:12])=[N+:7]([O-])[CH:8]=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3].C([O-])([O-])=[O:14].[K+].[K+]>CC(OC(C)=O)=O.CO>[CH2:1]([C:5]1[C:6]([CH2:12][OH:14])=[N:7][CH:8]=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]3-Isobutyl-2-methyl-pyridine-1-oxide (821 mg, 4.97 mmol) was dissolved in Ac2O (10 mL) and stirred at 100° C. for 16 hours. The Ac2O was removed under reduced pressure and the resulting brown oil was quenched with saturated NaHCO3 (30 mL) and extracted with CH2Cl2 (6×50 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo to yield a brown oil. Purification was avoided at this step due to the identical Rf values of the two products formed. The brown oil was dissolved in MeOH (20 mL) and powdered K2CO3 (2.05 g) was added. The mixture was stirred at room temperature for 2.5 hours. The solid was removed via suction filtration and the filtrate was concentrated in vacuo to give a brown oil. Purification via column chromatography on silica gel (CH2Cl2:MeOH, 95:5, v/v) afforded (3-isobutyl-pyridin-2-yl)-methanol as a yellow oil (383 mg, 78%, 2-steps). 1H NMR (CDCl3) δ 0.93 (d, 6H, J=6.0 Hz), 1.86 (m, 1H), 2.38 (d, 2H, J=6.0 Hz), 4.73 (s, 2H), 4.90 (br s, 1H), 7.18 (dd, 1H, J=9.0, 3.0 Hz), 7.45 (d, 1H, J=9.0), 8.41 (d, 1H, J=6.0 Hz).
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