Sodium Azide → [3-(Azidomethyl)oxetan-3-yl]methanol

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A solution of sodium azide (2.07 g, 0.0317 mol), 3-bromomethyl-3-hydroxymethyloxetane (5.0 g, 0.028 mol) and tetra-n-butylammonium bromide (0.0978 g, 0.3 mmol) in water (14 mL) was heated for 3 h at 104°-107° C. The solution was cooled and was extracted with ethyl ether (5×20 mL). The combined extracts were evaporated to give 1.92 g (49%) of 3-azidomethyl-3-hydroxymethyloxetane, essentially pure by glc analysis, as an oil. NMR: 1H NMR: 3.70 (s, 2H), 3.84 (d, J=4.9 Hz, 2H), 4.44 (s, 4H); 13C NMR: 44.283, 53.852, 64.073, 76.227.

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