Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][CH2:14][C:15]([CH3:18])([CH3:17])[N:16]=2)=[CH:8][CH:7]=1.[I-].[Na+].[Na].[CH3:22][CH:23]1[CH2:27][CH2:26][CH:25]([CH3:28])[NH:24]1>C(#N)C.C(OCC)(=O)C.O>[CH3:22][CH:23]1[CH2:27][CH2:26][CH:25]([CH3:28])[N:24]1[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][CH2:14][C:15]([CH3:18])([CH3:17])[N:16]=2)=[CH:8][CH:7]=12-[4-(3-chloropropoxy)phenyl]-4,4-dimethyl-4,5-dihydro-1,3-oxazole ax10 (500 mg, 1.87 mmol, 1 eq), sodium iodide (0.56 mg, 3.74 mmol, 2 eq), sodium hydrogenocarbonate (0.31 mg, 3.74 mmol, 2 eq) and 2,5-dimethylpyrrolidine (0.24 ml, 2.8 mmol, 1.5 eq) are stirred at reflux overnight in dry acetonitrile (10 ml). Water and ethyl acetate are added to the mixture and the layers are separated. The organic layer is dried with brine, sodium sulfate and evaporated under vacuum. Flash chromatography over silica with ethyl acetate as the eluent gives 0.253 g of 2-(4-{3-[2,5-dimethylpyrrolidin-1-yl]propoxy}phenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole 18 as a free base.
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