[CH2:1]([CH:3]([CH2:9][CH3:10])[C:4](=[O:8])[CH2:5][C:6]#[N:7])[CH3:2].[C:11]([O:14][C:15](=O)[CH3:16])(=O)[CH3:12].C(OCC)(OCC)(OCC)C>C(OCC)(=O)C.O>[CH2:1]([CH:3]([CH2:9][CH3:10])[C:4]([C:5](=[C:11]([O:14][CH2:15][CH3:16])[CH3:12])[C:6]#[N:7])=[O:8])[CH3:2]A mixture of 4-ethyl-3-oxo-hexanenitrile (1.013 g, 7.28 mmol), acetic anhydride (1.5 ml) and triethyl orthoacetate (1.240 g, 7.64 mmol) was heated to reflux overnight. The reaction mixture was taken up in ethyl acetate and water. The brine and the ethyl acetate layer were separated. The organic layer was dried and concentrated to give 1.262 g of dry oil which was used directly for the next reaction. 1H NMR (CDCl3): 0.8-1.0(m,6H), 1.44(t,3H), 1.4-1.8(m,4H), 2.61(s,3H), 3.03(m,1H), 4.28(q, 2H)ppm.
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