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

HRID 2099683Notes

Reaction equation

HRID 2099683 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]decaneYield 100.9%

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 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%).

Workup

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

Sources & evidence

ORD record
ord-55bef0ee2a9c41e4942fe424dfbdfb0c
Source dataset
uspto-grants-2009_08
Patent number
US07569600B2

Reaction notes

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