[Br:1][C:2]1[CH:3]=[CH:4][C:5](Cl)([CH3:8])[NH:6][CH:7]=1.[CH2:10]([OH:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[K+]>C1(C)C=CC=CC=1.C1OCCOCCOCCOCCOCCOC1>[CH2:10]([O:17][C:7]1[C:2]([Br:1])=[CH:3][CH:4]=[C:5]([CH3:8])[N:6]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1step 1—A mixture of 5-bromo-2-chloro-2-picoline (4.855 g, 23.51 mmol), benzyl alcohol (2.60 mL, 25.12 mmol), KOH (2.93 g, 52.32 mmol), and 18-crown-6 ether (0.34 g, 1.29 mmol) in toluene (30 mL) was refluxed overnight. The reaction was cooled to RT, diluted with ice water and extracted with EtOAc. The organic extract was washed with brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified by SiO2 chromatography eluting with 2% EtOAc/hexanes to afford 5.006 g (78%) of 2-benzyloxy-3-bromo-6-methyl-pyridine (58) as a colorless oil.
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