Sodium Azide → Ethyl 3-azido-2-hydroxypropanoate

HRID 1453836Notes

Reaction equation

Br[CH2:2][CH:3]([OH:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[N-:10]=[N+:11]=[N-:12].[Na+]>CCO.O>[N:10]([CH2:2][CH:3]([OH:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[N+:11]=[N-:12]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of ethyl 3-bromo-2-hydroxypropanoate (22.1 g, 112.0 mmol) in EtOH/H2O (1:1) was added sodium azide (10.9 g, 168.0 mmol). The reaction was stirred and heated to 90° C. for 3 days. The EtOH was removed in vacuo and the remaining aqueous solution was extracted with CHCl3 several times. The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to afford the azide as an orange oil. 1H NMR (400 MHz, d6-DMSO) δ 5.96 (d, J=5.6 Hz, 1H), 4.31-4.28 (m, 1H), 4.19-4.08 (m, 2H), 3.51-3.40 (m, 2H), 1.28-1.17 (m, 3H).

Workup

customThe EtOH was removed in vacuo
extractionthe remaining aqueous solution was extracted with CHCl3 several times
dry with materialThe combined organic extracts were dried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-b2e2702fe4a14ab487c9f275c9e007fd
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07476666B2

Reaction notes

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