Sodium Azide → 2-(2-Azidoethoxy)oxane

HRID 2067192Notes

Reaction equation

HRID 2067192 reaction equation
Br[CH2:2][CH2:3][O:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][O:6]1.[N-:11]=[N+:12]=[N-:13].[Na+].CCOC(C)=O.O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[N:11]([CH2:2][CH2:3][O:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][O:6]1)=[N+:12]=[N-:13]

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 22728543Water ethylacetate

Product 1

HCID 600742872-(2-Azidoethoxy)oxane

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(2-bromo-ethoxy)-tetrahydro-pyran (1.00 mL, 6.62 mmol), NaN3 (4.34 g, 66 mmol) and tetrabutylammonium iodide (245 mg, 0.66 mmol) in DMF (7.0 mL) was stirred at RT for 18 h. The reaction mixture was poured into a mixture of EtOAc/water. The organic phase was washed with water, brine and then dried (MgSO4), filtered and concentrated in vacuo to give the crude product. The crude product was purified by continuous gradient flash chromatography using EtOAc/petroleum ether (40-60) 0:100 to 20:80 as the eluent to afford the title compound as colourless oil.

Workup

  1. washThe organic phase was washed with water, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give the crude product
  6. customThe crude product was purified by continuous gradient flash chromatography

Sources & evidence

ORD record
ord-ee53d6f9a5bf41f3b026d03b2a71bebc
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

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