Sodium Azide → Acetic acid 3-azido-propyl ester

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.

1. temperatureto reflux for 18 hours
2. concentrationconcentrated to half of its volume
3. customThe reaction mixture was partitioned with water and ethyl acetate
4. washThe organic layer was washed with water
5. dry with materialdried with Na2SO4
6. filtrationfiltered
7. customthe solvent evaporated in vacuo

ORD record

ord-180f395095e940d0826f402dffde1c93

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08741916B2