[N:1]([CH2:4][CH:5]([OH:10])[CH:6]([OH:9])[CH2:7][OH:8])=[N+:2]=[N-:3].CO[C:13](OC)([CH3:15])[CH3:14].S(=O)(=O)(O)O.[OH-].[Na+]>CC(C)=O>[N:1]([CH2:4][CH:5]([CH:6]1[CH2:7][O:8][C:13]([CH3:15])([CH3:14])[O:9]1)[OH:10])=[N+:2]=[N-:3]A solution of 14.71 g of 4-azido-1,2,3-butanetriol in 30 ml of acetone is combined with 13.95 g of 2,2-dimethoxypropane, as well as 0.1 ml of concentrated sulfuric acid. The mixture is stirred overnight at room temperature, neutralized with 2N sodium hydroxide solution, and concentrated to dryness under vacuum. The residue is distilled with a water-jet aspirator. 2-Azido-(2,2-dimethyl-1,3-dioxolan-4-yl)ethanol passes over as a colorless oil at 130°-132° C./13 mm. Yield: 11.79 g (63% of theory).
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