Sodium Azide → 8-Azido-1,4-dioxaspiro[4.5]decane

HRID 1190061

Reaktionsgleichung

Reaktionsgleichung von HRID 1190061
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8](OS(C)(=O)=O)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[N-:16]=[N+:17]=[N-:18].[Na+]>CN(C=O)C.[Cl-].[Na+].O>[N:16]([CH:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1)=[N+:17]=[N-:18]

Komponenten

5

Edukt 2

HCID 33557Sodium AzideHCID 149667411,4-Dioxaspiro(4.5)decan-8-yl methanesulfonate

Produkt 1

HCID 574240948-Azido-1,4-dioxaspiro[4.5]decaneAusbeute 100,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of methanesulfonic acid 1,4-dioxa-spiro[4.5]dec-8-yl ester (2.80 g, 11.9 mmol) and sodium azide (3.86 g, 59.3 mmol) in 50 mL of dry DMF was stirred for 20 h at 100° C. under nitrogen. The final mixture was cooled to room temperature dilute with brine and extracted with three portions of ether. The organic portions were combined, dried over Na2SO4 and concentrated to give 8-azido-1,4-dioxa-spiro[4.5]decane (2.2 g, 100%).

Aufarbeitung

  1. extractionextracted with three portions of ether
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-cb31b2c05cf44bd1aaaeb70cfa80f4cb
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08674118B2

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