[N+:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[CH2:7][CH2:6]2)#[C-:2].[Si:13]([O:20][NH2:21])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].S(O)(C1C=CC(C)=CC=1)(=O)=O.O>C(Cl)(Cl)Cl>[Si:13]([O:20][N:21]=[C:8]1[C:9]2[C:5](=[CH:4][C:3]([N+:1]#[C-:2])=[CH:11][CH:10]=2)[CH2:6][CH2:7]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]5-isocyano-2,3-dihydroinden-1-one (6) (3.00 g, 19.1 mmol) was combined with 1.4 eq. of O-(tert-butyldimethylsilyl)hydroxylamine (3.94 g, 26.7 mmol) and TsOH-H2O (0.363 g, 1.91 mmol) in 100 mL CHCl3 and heated to reflux overnight. TLC showed a small amount of remaining starting material and two non-polar spots corresponding to the oxime isomers. The reaction mixture was filtered and concentrated to a brown semi-solid, then purified immediately by loading onto a silica column with DCM and eluting with 1% MeOH/DCM to give 4.1 g (75%) of 5-isocyano-2,3-dihydroinden-1-one O-tert-butyldimethylsilyl oxime (7).
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