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

HRID 1195354

Reaktionsgleichung

Reaktionsgleichung von HRID 1195354
[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-63ab5e877aee4f5ab1adac99d2e56640
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05110940

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