Sodium hydride → (tert-Butylsulphinyl)-2-[4-(propylsulphonyl)phenyl]aziridine

反応式

[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[CH3:9][C:10]([S:13](/[N:15]=[CH:16]/[C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24])=[CH:19][CH:18]=1)=[O:14])([CH3:12])[CH3:11]>CS(C)=O>[C:10]([S:13]([N:15]1[CH2:4][CH:16]1[C:17]1[CH:18]=[CH:19][C:20]([S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24])=[CH:21][CH:22]=1)=[O:14])([CH3:9])([CH3:11])[CH3:12]

参加物

実験手順

Sodium hydride (0.33 g of a 60% dispersion in mineral oil, 8.37 mmol) was added portionwise to a stirred solution of trimethylsulphoxonium iodide (1.84 g, 8.37 mmol) in DMSO (30 mL). The mixture was stirred at room temperature for 1 h by which time effervescence had ceased and the mixture was mostly clear. 2-Methyl-N-{(1E)-[4-(propylsulphonyl)phenyl]methylene}propane-2-sulphinamide (1.76 g, 5.58 mmol) was added and the resulting solution stirred at room temperature overnight. The reaction mixture was quenched by addition of water and the product extracted into ethyl acetate (×2). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated to give the title compound (1.44 g, 88% yield).