Sodium Azide → Acetic acid 3-azido-propyl ester

Participants

Reaction Steps

Acetic acid 3-bromo-propyl ester (6.7 g, 37 mmol) was suspended in water (50 mL) and tert-butanol (20 mL). To the resulting mixture was then added sodium azide (2.76 g, 42.6 mmol) and the reaction mixture was heated to reflux for 18 hours, then concentrated to half of its volume. The reaction mixture was partitioned with water and ethyl acetate. The organic layer was washed with water, dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield the acetic acid 3-azido-propyl ester (3.16 g) as an oil which used in the next step without further purification.

Provenance & Evidence