Ethyl Acetate → HCID 178424789, Verbindung

HRID 337267Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 337267
[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([CH3:15])=[C:8]([CH2:12][C:13]#[N:14])[CH:9]=[CH:10][CH:11]=1.[N-:21]=[N+:22]=[N-:23].[Na+].[Cl-].[NH4+].C(OCC)(=O)C>CN(C=O)C.CCCCCC>[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([CH3:15])=[C:8]([CH:9]=[CH:10][CH:11]=1)[CH2:12][C:13]1[NH:23][N:22]=[N:21][N:14]=1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 669591112-(3-(2,6-Dimethylbenzyloxy)-2-methylphenyl)acetonitrile

Produkt 1

HCID 178424789HCID 178424789, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 2-(3-(2,6-Dimethylbenzyloxy)-2-methylphenyl)acetonitrile (Step E, 2.70 g, 10.19 mmol), sodium azide (0.795 g, 12.23 mmol) and ammonium chloride (0.653 g, 12.22 mmol) in dry DMF (20 ml) was heated under argon at 90° C. for 16 hours or until all the starting material is consumed, the reaction mixture was cooled, diluted with water and extracted with EtOAc (30 ml×4). The combined organic layer was washed with brine, dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (chloroform:methanol 92.5:7.5) to give semi solid product. The semi solid was stirred with 1:2 ethyl acetate:hexane (15 ml) for 10 minutes, and filtered to give product as a white solid.

Aufarbeitung

  1. customis consumed
  2. temperaturethe reaction mixture was cooled
  3. additiondiluted with water
  4. extractionextracted with EtOAc (30 ml×4)
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by flash chromatography on a silica gel column (chloroform:methanol 92.5:7.5)
  10. customto give semi solid product
  11. filtrationfiltered
  12. customto give product as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-4351dcc52dc5420b8cca9a5315459bf2
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889724B2

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