[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH2:13][CH3:14])[C:11]#[N:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(O)CCC.[C:20]([O:24][CH3:25])(=[O:23])[CH:21]=[CH2:22].CC(C)([O-])C.[K+]>C(O)(C)(C)C>[C:11]([C:10]([C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)([CH2:13][CH3:14])[CH2:22][CH2:21][C:20]([O:24][CH3:25])=[O:23])#[N:12]
A mixture of 2-(4-nitrophenyl)butyronitrile (10.0 g), butanol (10 ml) and methyl acrylate (5.2 ml) was cooled to 10° C. in a 100 ml 3-necked round-bottomed flask, equipped with a magnetic follower. A solution of potassium tert-butoxide (0.6 g) in tert-butanol (10 ml) was added dropwise, maintaining the temperature at approximately 10° C. (solution turns purple). After addition was complete, the mixture was allowed to reach ambient temperature and then stirred for a further 2 hours. The reaction was worked-up by partitioning between diethyl ether (400 ml) and 1M KH2PO4 (400 ml). The ether layer was washed with water (50 ml), dried (MgSO4) and concentrated under reduced pressure to yield methyl 4-cyano-4-(4-nitrophenyl)hexanoate (14.1 g, 99%) as an orange oil.
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