[CH2:1]([N:8]([CH2:15][CH2:16]Cl)[CH2:9][C:10]1[CH:14]=[CH:13][O:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[OH-].[Na+]>O1CCCC1.CCCCCC>[CH2:1]([N:8]1[CH2:15][CH2:16][C:11]2[O:12][CH:13]=[CH:14][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1To a solution of 0.209 g (0.837 mmol) of N-benzyl-N-(3-furylmethyl)-2-chloroethylamine in 50 ml of tetrahydrofuran, 1.05 ml (1.67 mmol) of 1.6 M n-butyl lithium in hexane was added under ice-cooling, followed by stirring at room temperature for 2 hours. The reaction mixture was poured into aqueous sodium hydroxide and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=9/1) to yield 5-benzyl-4,5,6,7-tetrahydrofuro[3,2-c]pyridine.
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