[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([C:11]3[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:10]=3[O:9][CH2:8]2)[CH2:4][CH2:3]1.ClC1C=CC(O[CH2:25][C:26]#[N:27])=CC=1.CC(C)([O-])C.[K+].Cl>CN(C=O)C.O>[C:26]([CH2:25][C:14]1[C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]2[C:5]3([CH2:8][O:9][C:10]=2[CH:15]=1)[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)#[N:27]
2,3-Dihydro-1-methyl-5-nitrospiro[benzofuran-3,4'-piperidine](D4, 0.70 g, 2.8 mmol) and 4-chlorophenoxyacetonitrile (0.90 g, 5.4 mmol) were dissolved in dry DMF (15 ml) and added to potassium t-butoxide (1.60 g, 14.3 mmol). The mixture was stirred under Ar for 6h, diluted with water (150 ml), acidified (5M HCl) and washed with ethyl acetate. It was then basified (saturated K2CO3 solution) and extracted with ethyl acetate. This extract was dried (Na2SO4) and evaporated to give the title compound (0.35 g, 43%) still containing some spirocyclic starting material (ca 30%, NMR).
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