Sodium Azide → 3-Azidomethyl-3-phenoxymethyloxetane

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Reaction Steps

A mixture of 3-chloromethyl-3-phenoxymethyloxetane (20.0 g, 44 mmol), sodium azide (7.35 g, 113 mmol), sodium bicarbonate (0.53 g, 6.3 mmol), tetra-n-butylammonium bromide (0.653 g, 2.0 mmol) and water (41 mL) was heated at about 109° C. to about 113° C. for 16 h. The mixture was cooled and separated. The organic layer was washed with brine solution, diluted with methylene chloride and filtered through a pad of alumina. The solvent was evaporated to give 17.9 g (87%) of 3-azidomethyl-3-phenoxymethyloxetane as an oil that was pure by glc and NMR analysis. NMR: 1H NMR: d 3.71 (s, 2H), 4.07 (s, 2H), 4.42 & 4.46 (AB, J=6.2 Hz, 4H), 6.83-7.21(m, 5H); 13C NMR: d 43.36,53.88, 68.84, 76.18, 114.47, 121.31, 129.50, 158.45; glc Rt=8.13 min.

Provenance & Evidence