[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[O:12][CH2:13][C:14]#[N:15].O.C(Cl)Cl.CO>C1COCC1>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[O:12][CH2:13][CH2:14][NH2:15]To a cold (0° C.) suspension of LiAlH4 (1.73 g, 45.6 mmol) in anhydrous THF (72 ml), was added dropwise a solution of (3,4-dimethoxy-phenoxy)-acetonitrile (5.88 g, 30.4 mmol) in anhydrous THF (42 ml). The resulting mixture was allowed to warm-up and stirred at RT for 20 h under nitrogen. The reaction mixture was combined with a mixture of H2O/2N NaOH(aq) (4/1) to destroy the excess of LiAlH4. The white suspension was filtered and the solid was washed with CH2Cl2. The combined organic phases were dried over anhydrous MgSO4, filtered and concentrated to give a crude oil. Flash chromatography (CH2Cl2/MeOH: 9/1) gave the title product (4.65 g, 77%).
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