Sodium Azide → 2-(2-Azidoethoxy)oxane

HRID 2067192Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2067192
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]

Komponenten

6

Edukt 3

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

Produkt 1

HCID 600742872-(2-Azidoethoxy)oxane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ee53d6f9a5bf41f3b026d03b2a71bebc
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08293772B2

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