[N:1]([CH:4]([CH3:7])[CH2:5][OH:6])=[N+:2]=[N-:3].[H-].[Na+].Cl[CH2:11][C:12](=[O:19])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]>O1CCCC1>[N:1]([CH:4]([CH3:7])[CH2:5][O:6][CH2:11][C:12](=[O:19])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N+:2]=[N-:3]A solution of the 2-azidopropan-1-ol (10.1 g) in tetrahydrofuran (100 ml) was added over two minutes to a stirred, ice-cooled suspension of sodium hydride (6.6 g; 80% dispersion in oil) in tetrahydrofuran (50 ml). The mixture was stirred for 15 minutes with ice-cooling and then treated over 20 minutes with a solution of ethyl 4-chloroacetoacetate (16.4 g) in tetrahydrofuran (150 ml). The mixture was stirred at room temperature for 16 hours and evaporated. The residue was diluted with water, washed twice with ether, acidified with 2M hydrochloric acid, and extracted three times into ether. The combined ether extracts were dried (Na2SO4) and evaporated to give crude ethyl 4-(2-azidoprop-1-oxy)acetoacetate (20 g), used directly.
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