Hydrochloric Acid → HCID 86722711, Verbindung

HRID 1480495Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1480495
[CH2:1]([OH:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[CH:8].[N:10]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[N+:11]=[N-:12].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].Cl.[Na+].[Cl-]>CC(O)(C)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.O>[CH2:13]([N:10]1[CH:8]=[C:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:9])[N:12]=[N:11]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 12152Benzyl azideHCID 701007-Octyn-1-olHCID 23667548Sodium Ascorbate

Produkt 1

HCID 86722711HCID 86722711, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8895Cupric acetateKatalysatorHCID 962WaterLösungsmittelHCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

Oct-7-yn-1-ol (0.948 g, 7.51 mmol) was dissolved in tBuOH (100 mL) and water (100 mL) to give a colourless solution. (Azidomethyl)benzene (1 g, 7.51 mmol), copper (II) acetate (0.136 g, 0.751 mmol) and sodium L-ascorbate (0.298 g, 1.502 mmol) were added. The reaction was left to stir overnight at room temperature, then was acidified to pH1 using 6M HCl. The mixture was saturated with solid NaCl and concentrated under pressure to give a green slurry. This was extracted with EtOAc, and the organics were separated, dried over MgSO4, and concentrated under reduced pressure. The resulting oil was dissolved in methanol and stirred with celite/charcoal. The mixture was filtered and the filtrate concentrated under reduced pressure to give the title compound.

Aufarbeitung

  1. waitThe reaction was left
  2. concentrationconcentrated under pressure
  3. customto give a green slurry
  4. extractionThis was extracted with EtOAc
  5. customthe organics were separated
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. dissolutionThe resulting oil was dissolved in methanol
  9. stirringstirred with celite/charcoal
  10. filtrationThe mixture was filtered
  11. concentrationthe filtrate concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c4036fd7852b4943995b0f291e578add
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09409895B2

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