1,5-Dimethyltetrazole → 1,1-Bis(2,4-dimethylphenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethanol

HRID 974472

Reaktionsgleichung

Reaktionsgleichung von HRID 974472
[CH3:1][N:2]1[C:6]([CH3:7])=[N:5][N:4]=[N:3]1.C([Li])CCC.[CH3:13][C:14]1[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:15]=1[C:16]([C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=1[CH3:25])=[O:17]>O1CCCC1>[CH3:25][C:19]1[CH:20]=[C:21]([CH3:24])[CH:22]=[CH:23][C:18]=1[C:16]([C:15]1[CH:26]=[CH:27][C:28]([CH3:30])=[CH:29][C:14]=1[CH3:13])([OH:17])[CH2:7][C:6]1[N:2]([CH3:1])[N:3]=[N:4][N:5]=1

Komponenten

5

Edukt 3

HCID 788251,5-DimethyltetrazoleHCID 12274022Bis(2,4-dimethylphenyl)methanoneHCID 178418339Butyllithium

Produkt 1

HCID 147239461,1-Bis(2,4-dimethylphenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethanolAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

A solution of 1,5-dimethyltetrazol (8.9 g, 91.0 mmoles) in 100 mL of dry tetrahydrofuran at -60° C. was treated with n-butyl lithium (48 mL of 1.89M solution, 91.0 mmoles). After stirring for 20 minutes, 2,2',4,4'-tetramethylbenzophenone (18 g, 76 mmoles) [prepared by the procedure described in J. Am. Chem. Soc., 81, 4858 (1959)] in 50 mL dry tetrahydrofuran was added and the solution was stirred for 1 hour during which time it was allowed to warm to -20° C. The reaction was quenched with 1N HCl, then extracted with chloroform. The combined organic extracts were dried (MgSO4) and evaporated to give 22 g of the title compound; m.p.=175°-177° C.

Aufarbeitung

  1. stirringthe solution was stirred for 1 hour during which time it
  2. customThe reaction was quenched with 1N HCl
  3. extractionextracted with chloroform
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-993db651a548428c82b5a92be3b7db66
Quelldatensatz
uspto-grants-1991_11
Patentnummer
US05068346

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