Potassium Carbonate → 1-(benzyloxymethyl)-2H-tetrazole

HRID 1888108

Reaktionsgleichung

Reaktionsgleichung von HRID 1888108
[NH:1]1[CH:5]=[N:4][N:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C=O)C.C(OCC)C>[CH2:15]([O:14][CH2:13][N:2]1[N:3]=[N:4][CH:5]=[N:1]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH2:15]([O:14][CH2:13][N:1]1[CH:5]=[N:4][NH:3][NH:2]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 137983Benzyl chloromethyl ether2×HCID 178418441HCID 178418441, Verbindung

Produkt 2

HCID 107263402-((benzyloxy)methyl)-2H-tetrazoleAusbeute 44 %HCID 672998451-(benzyloxymethyl)-2H-tetrazoleAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A suspension of 1-H-tetrazole (2.0 g, 28.5 mmol) and potassium carbonate (5.9 g, 42.7 mmol) in DMF (30 mL) was treated with benzyl chloromethyl ether (5.36 g, 34.2 mmol), and the mixture was stirred for 4 hours. Analysis by LC/MS indicated that the reaction was not complete, so the reaction was treated with benzyl chloromethyl ether (0.5 g, 3.19 mmol) and stirred for about 16 h. After this time, the mixture was filtered, and the filtrate was concentrated in vacuo to yield a residue. The residue was diluted with diethyl ether (200 mL), washed 5× with water (50 mL), once with brine, dried over sodium sulfate, and concentrated in vacuo to yield a residue. The residue was purified over a 6×20 mm silica gel column, eluting with 20% then 30% ethyl acetate/hexanes to yield the title compound (2.39 g, 44% yield), and 1-(benzyloxymethyl)-2H-tetrazole (2.56 g, 47% yield).

Aufarbeitung

  1. stirringstirred for about 16 h
  2. filtrationAfter this time, the mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto yield a residue
  5. washwashed 5× with water (50 mL)
  6. dry with materialonce with brine, dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto yield a residue
  9. customThe residue was purified over a 6×20 mm silica gel column
  10. washeluting with 20%

Quellen und Nachweise

ORD-Eintrag
ord-2048772766ec48038c53957ace20d300
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501782B2

Verknüpfte Notizen

Wird geladen…