Sodium Azide → 4-(Azidomethyl)-2,2-dimethyl-1,3-dioxolane

Participants

Reaction Conditions

Reaction Steps

To a solution of (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate (5.73 g, 20.00 mmol) in DMF (40 mL) was added sodium azide (2.6 g, 40.00 mmol) and the reaction mixture was stirred at 80° C. for 18 hr. The solvent was evaporated under reduced pressure, diluted with water (100 mL) and extracted 3 times with ethyl acetate (3×75 mL), which was consecutively washed with H2O (100 mL), brine (100 mL) and finally dried over MgSO4. The solvent was removed under vacuum to afford 2.2 g of 13 as brown oil (76% yield). 1H NMR (CDCl3, 400 MHz) δ: 4.21-4.27 (m, 1H), 4.02 (dd, J=6.4, 8.4 Hz, 1H), 3.74 (dd, J=6.0, 8.4 Hz, 1H), 3.36 (dd, J=4.8, 12.8 Hz, 1H), 3.26 (dd, J=5.6, 12.8 Hz, 1H), 1.43 (s, 3H), 1.33 (s, 3H).

Provenance & Evidence