C([O:3]P(OCC)OCC)C.[OH-].[K+].[CH3:13][N:14]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][N:16]=[C:15]1[CH:22]([CH3:24])[CH3:23].O=O>O=P(N(C)C)(N(C)C)N(C)C.O.C(O)(=O)C>[OH:3][C:22]([C:15]1[N:14]([CH3:13])[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][N:16]=1)([CH3:24])[CH3:23]
A total of 11.2 ml of triethylphosphite and 6 g of powdered potassium hydroxide were added to a solution of 8.5 g of 1-methyl-2-isopropyl-5-nitroimidazole in 40 ml of hexametapol while cooling in an ice-bath. While the solution was further cooled with ice, oxygen was conducted through the solution with vigorous stirring. After 2.5 hours, 6.1 ml of glacial acetic acid were added and the mixture was then poured into 600 ml of water and extracted four times with 150 ml portions of ether. The ether extracts were washed with a small amount of water, evaporated on a rotary evaporator and finally dried at 85°/0.5 Torr. The residue was crystallized from 15 ml of isopropyl ether. There were obtained 2.0 g of 2-(2-hydroxy-2-propyl)-1-methyl-5-nitroimidazole, melting point 102°-107°. The yield was 21.6%.
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