Sodium Azide → Ethyl 3-azido-2-hydroxypropanoate

HRID 1453836Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1453836
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]

Komponenten

4

Edukt 2

HCID 33557Sodium AzideHCID 13180684Ethyl 3-bromo-2-hydroxypropanoate

Produkt 1

HCID 10888191Ethyl 3-azido-2-hydroxypropanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 19096565Water ethanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-b2e2702fe4a14ab487c9f275c9e007fd
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07476666B2

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