C([Li])CCC.[CH3:6][O:7][C:8]1[C:17]([O:18][CH3:19])=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=1.CN(C)CCN(C)C.CN([CH:31]=[O:32])C>CCCCCC.CCOCC>[CH3:19][O:18][C:17]1[C:8]([O:7][CH3:6])=[CH:9][C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16]=1[CH:31]=[O:32]
n-Butyl lithium in hexane (1.6 N, 31.3 ml) was gradually added to a solution of 2,3-dimethoxynaphthalene (9.4 g) and N,N,N′,N′-tetramethylethylenediamine (7.4 ml) in ether (150 ml) under argon at 0° C. The reaction mixture was stirred at room temperature for two hours, cooled to 0° C. and DMF (7.3 g) in ether (20 ml) added. The reaction mixture was stirred at room temperature overnight and poured in ice water. The product was extracted with ether, washed with water, dried, evaporated and recrystallized from ether. Yield: 4.2 g.
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