Dimethylformamide → 1-Methyl-4-phenyl-1H-1,2,3-triazole-5-carbaldehyde

HRID 402342Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 402342
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]=[N:3]1.[Li]CCCC.CN([CH:21]=[O:22])C.[Cl-].[NH4+]>C1COCC1>[CH3:1][N:2]1[C:6]([CH:21]=[O:22])=[C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:4]=[N:3]1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 1130966315965-36-3HCID 178418339Butyllithium

Produkt 1

HCID 735550571-Methyl-4-phenyl-1H-1,2,3-triazole-5-carbaldehydeAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-75 °C

Versuchsvorschrift

To a solution of 1-methyl-4-phenyl-1H-[1,2,3]triazole (165 mg, 1.04 mmol) in THF (5.2 mL) was added n-BuLi (1.6 M in hexane, 777 μL, 1.24 mmol) dropwise at −75° C. under Argon. The resulted orange solution was stirred at −75° C. for 40 min, then DMF (104 μL, 1.35 mmol) was added dropwise at −75° C. and the reaction mixture was allowed to warm up to room temperature over 1 h. The mixture was then poured into saturated ammonium chloride solution and extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, 0 to 50% ethyl acetate in heptane) afforded the title compound (131 mg, 68%) as a white solid. MS: m/e=187.0 [M]+.

Aufarbeitung

  1. temperatureto warm up to room temperature over 1 h
  2. extractionextracted with ethyl acetate
  3. washthe combined organic extracts washed with brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by chromatography (silica, 0 to 50% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-ee94013090da459791dcd4df31f4e82a
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08742097B2

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