[Li+].CC([N-]C(C)C)C.[C:9](#[N:13])[CH:10]([CH3:12])[CH3:11].[Cl:14][CH2:15][CH2:16][O:17][CH2:18]Cl.O>C1COCC1.CCOCC>[Cl:14][CH2:15][CH2:16][O:17][CH2:18][C:10]([CH3:12])([CH3:11])[C:9]#[N:13]
To a solution of LDA (0.14 mol) in 100 mL THF at −30° C. under N2 was added isobutyronitrile (9.7 g, 0.14 mol) in 40 mL THF, dropwise over 20 min. After 20 min, a solution of 1-chloro-2-(chloromethoxy)ethane (18.1 g, 0.14 mol) in 50 mL THF was added dropwise and the temperature was allowed to gradually rise to room temperature and the reaction mixture stirred for 5 h. This was treated with 200 mL of water and Et2O and the layers separated. The aqueous layer was extracted further with Et2O. The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated to leave 23 g of crude product as a yellow oil. This was purified by silica gel chromatography using 9:1 hexanes/CH2Cl2 to 4:1 hexanes/CH2Cl2 as eluents. This yielded 7.4 g (32%) of the title compound as an oil. 1H NMR (300 MHz, CDCl3) δ: 1.33 (s, 6H), 3.43 (s, 2H), 3.61 (t, J=5.7 Hz, 2H), 3.77 (t, J=5.9 Hz, 2H). LC/MS (M+H): 162.
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