[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:14][CH2:15][C:16]([CH3:21])([C:19]#[N:20])[C:17]#[N:18])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>C(OCC)C>[CH2:7]([O:14][CH2:15][C:16]([CH3:21])([CH2:19][NH2:20])[CH2:17][NH2:18])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1LiAlH4 (3.22 g; 84.84 mmol; 3.0 equiv.) was suspended in 30 mL dry diethylether and cooled with an ice bath. A solution of 2-Benzyloxymethyl-2-methyl-malononitrile (5.72 g; 28.28 mmol; 1.0 equiv.) in 20 mL dry diethylether was added dropwise. The suspension was stirred at room temperature for 4 hours, and subsequently cooled with an ice bath. To this was added 3.22 mL H2O, 6.44 mL 2 M NaOH and 3.22 mL H2O. The precipitate was filtered off and washed with ether. The filtrate was concentrated under reduced pressure to yield 5.47 g (84%) of a colorless oil. 1H NMR (400 MHz, CDCl3) δ 0.84 (s, 3H), 2.59-2.69 (m, 4H) 3.29 (s, 2H), 4.49 (s, 2H), 7.24-7.39 (m, 5H).
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