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

HRID 244910Notes

Reaction equation

HRID 244910 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

HCID 574240948-Azido-1,4-dioxaspiro[4.5]decane

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

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 is stirred for 20 h at 100° C. under nitrogen. The final mixture is cooled to room temperature diluted with brine and extracted with three portions of ether. The organic portions are combined, dried over Na2SO4 and concentrated to give 8-azido-1,4-dioxa-spiro[4.5]decane.

Workup

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

Sources & evidence

ORD record
ord-6af41a6485674e8dae67ef40c30e6797
Source dataset
uspto-grants-2014_02
Patent number
US08658674B2

Reaction notes

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