[CH3:1][C:2](=[N:4][OH:5])[CH3:3].CC(C)([O-])C.[K+].[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([N+]([O-])=O)=[C:18]([CH:21]=1)[C:19]#[N:20]>CN(C=O)C.CCOCC>[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([O:5][N:4]=[C:2]([CH3:3])[CH3:1])=[C:18]([CH:21]=1)[C:19]#[N:20]In 400 ml of DMF was dissolved acetone oxime (34.5 g) followed by potassium t-butoxide (51 g). After this mixture had stirred for 30 minutes, 5-methoxy-2-nitro-benzonitrile (70 g) was added. After stirring overnight, the reaction was diluted with ether (~4 L) and filtered. The filtrate was washed with ethyl acetate and combined organics were washed with water (3×1.5 L), dried (MgSO4) and concentrated in vacuo. Preparative liquid chromatography (silica gel) eluting with 4:1 heptane/EtOAc yielded the expected product (10 g).
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