[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][N:7]2[C:12](=[O:13])[CH:11]=[CH:10][C:9]([CH:14]=[O:15])=[CH:8]2)=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C.CCOC(C)=O>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH:8]=[C:9]([CH2:14][OH:15])[CH:10]=[CH:11][C:12]2=[O:13])=[CH:16][CH:17]=1According to Scheme 16 Method B: A solution of 1-(4-chlorobenzyl)-6-oxo-1,6-dihydropyridine-3-carbaldehyde (1 eq, 1.41 mmol, 0.35 g, Example 10 Step 1) and DIBAL (3 eq, 4.20 mmol, 4.20 mL) in THF (5 mL) was stirred for 30 min. at −78° C. and 1 hour at room temperature. After addition of AcOEt, the reaction mixture was diluted with water. The organic layer washed with saturated NH4Cl solution, dried over Na2SO4, filtered through celite and evaporated. The resulting crude residue was purified by silica gel chromatography (AIT Flashsmart prepacked column 25 g SiO2) using CH2Cl2/MeOH 95/5 to afford 1-(4-chlorobenzyl)-5-(hydroxymethyl)pyridin-2(1H)-one (0.45 mmol, 0.11 g, 32%) as an orange oil.
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