[H-].[Na+].[CH3:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][C@H:16]([OH:18])[CH3:17])=[CH:9][CH:10]=2)[N:5]=1.[CH3:19]I>CN(C=O)C>[CH3:19][O:18][C@H:16]([CH3:17])[CH2:15][O:14][C:8]1[CH:7]=[C:6]2[C:11]([CH:12]=[CH:13][C:4]([CH3:3])=[N:5]2)=[CH:10][CH:9]=1To a stirred suspension of NaH (60% dispersion in oil, 95 mg, 2.4 mmol) in DMF (8 mL) was added dropwise a solution of (R)-1-(2-methylquinolin-7-yloxy)propan-2-ol (344 mg, 1.58 mmol) in DMF (4 mL) at 0° C. under nitrogen. The reaction mixture was stirred at 0° C. for 30 minutes. MeI (0.198 mL, 3.17 mmol) was added dropwise. The reaction was stirred at ambient temperature overnight. The reaction mixture was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with water and brine, dried and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (5:1 hexanes/EtOAc) to give (R)-7-(2-methoxypropoxy)-2-methylquinoline (185 mg, 51%).
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