Potassium Iodide → 2-(3-Azido-propoxy)-tetrahydro-pyran

HRID 2067194Notes

Reaction equation

HRID 2067194 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][O:7]1.[N-:12]=[N+:13]=[N-:14].[Na+].[I-].[K+].CCOCC.O>CN(C=O)C>[N:12]([CH2:2][CH2:3][CH2:4][O:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][O:7]1)=[N+:13]=[N-:14]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 33557Sodium AzideHCID 2549542-(3-Chloropropoxy)oxaneHCID 21584184Diethylether water

Product 1

HCID 866055212-(3-Azido-propoxy)-tetrahydro-pyran

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(3-chloro-propoxy)-tetrahydro-pyran (6.28 g, 35.2 mmol), NaN3 (11.4 g, 176 mmol) and potassium iodide (584 mg, 3.52 mmol) in DMF (50 mL) was stirred at RT for 18 h. The reaction mixture was poured into a mixture of Et2O/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 15:85 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-1d3a718c5972490fadf91bcc6d0fa9c3
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

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