Iodoethane → Ethyl 5-acetoxy-2-(5-methyltetrazol-1-yl)benzoate

HRID 598333Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 598333
C(=O)([O-])[O-].[Cs+].[Cs+].[C:7]([O:10][C:11]1[CH:12]=[CH:13][C:14]([N:20]2[C:24]([CH3:25])=[N:23][N:22]=[N:21]2)=[C:15]([CH:19]=1)[C:16]([OH:18])=[O:17])(=[O:9])[CH3:8].I[CH2:27][CH3:28]>CC(C)=O>[C:7]([O:10][C:11]1[CH:12]=[CH:13][C:14]([N:20]2[C:24]([CH3:25])=[N:23][N:22]=[N:21]2)=[C:15]([CH:19]=1)[C:16]([O:18][CH2:27][CH3:28])=[O:17])(=[O:9])[CH3:8]

Komponenten

5

Edukt 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 670509905-Acetoxy-2-(5-methyltetrazol-1-yl)benzoic acid

Produkt 1

HCID 67051123Ethyl 5-acetoxy-2-(5-methyltetrazol-1-yl)benzoateAusbeute 92,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

Cesium carbonate (176 g, 1.13 mol) was added to a solution of 5-acetoxy-2-(5-methyltetrazol-1-yl)benzoic acid (164 g, 0.620 mol) in 1.8 L of acetone. The mixture was stirred vigorously and iodoethane (116 g, 0.682 mol) diluted with 100 mL of acetone was added dropwise over a one-hour period. The reaction was stirred overnight at ambient temperature and was then concentrated under reduced pressure. The resulting solid was partitioned between dichloromethane and water. The aqueous fraction was extracted with dichloromethane and the combined organic fractions were dried over sodium sulfate, filtered, and concentrated to give 166 g of ethyl 5-acetoxy-2-(5-methyltetrazol-1-yl)benzoate as a brown oil.

Aufarbeitung

  1. additionwas added dropwise over a one-hour period
  2. stirringThe reaction was stirred overnight at ambient temperature
  3. concentrationwas then concentrated under reduced pressure
  4. customThe resulting solid was partitioned between dichloromethane and water
  5. extractionThe aqueous fraction was extracted with dichloromethane
  6. dry with materialthe combined organic fractions were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-46d1a8f35cee4a87af63120b17e146fa
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897597B2

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