Methanesulfonic Acid → 2-(2-Tert-butyl-tetrazol-5-yl)-benzaldehyde

HRID 1068926Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1068926
[NH:1]1[C:5]([C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[CH:8]=[O:9])=[N:4][N:3]=[N:2]1.[CH2:14]=[C:15]([CH3:17])[CH3:16].CS(O)(=O)=O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:15]([N:3]1[N:2]=[N:1][C:5]([C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[CH:8]=[O:9])=[N:4]1)([CH3:17])([CH3:16])[CH3:14]

Komponenten

6

Edukt 3

HCID 6395Methanesulfonic AcidHCID 8255IsobutyleneHCID 178519511HCID 178519511, Verbindung

Produkt 1

HCID 211906522-(2-Tert-butyl-tetrazol-5-yl)-benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In an autoclave, 6.4 g (36.7 mmol) of 2-(tetrazol-5-yl)-benzaldehyde (Step 61.1) in 50 ml of toluene are heated at 110° C. for 1.5 hours with ≈3 g of isobutene and 0.432 ml of methanesulfonic acid. When cold the reaction mixture is diluted with 300 ml of ethyl acetate, washed four times with water and once with brine, dried (Na2SO4) and concentrated by evaporation. Column chromatography (SiO2; hexane/ethyl acetate=4:1) and crystallization from hexane with a small amount of diethyl ether at −20° C. yield 2-(2-tert-butyl-tetrazol-5-yl)-benzaldehyde; TLC: Rf=0.36 (hexane/ethyl acetate=10:1).

Aufarbeitung

  1. washwashed four times with water
  2. dry with materialonce with brine, dried (Na2SO4)
  3. concentrationconcentrated by evaporation
  4. customColumn chromatography (SiO2; hexane/ethyl acetate=4:1) and crystallization from hexane with a small amount of diethyl ether at −20° C.

Quellen und Nachweise

ORD-Eintrag
ord-108f0cb0719a4ac59690329c82670420
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06251911B1

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