Carbon Dioxide → 2-(3-Hexyl-phenyl)-5-iodo-3-methyl-3H-imidazole-4-carboxylic acid

HRID 545328

Reaktionsgleichung

Reaktionsgleichung von HRID 545328
[CH2:1]([C:7]1[CH:8]=[C:9]([C:13]2[N:14]([CH3:20])[C:15](I)=[C:16]([I:18])[N:17]=2)[CH:10]=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C([Li])CCC.[C:26](=[O:28])=[O:27]>C1COCC1>[CH2:1]([C:7]1[CH:8]=[C:9]([C:13]2[N:14]([CH3:20])[C:15]([C:26]([OH:28])=[O:27])=[C:16]([I:18])[N:17]=2)[CH:10]=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Komponenten

5

Edukt 3

HCID 280Carbon DioxideHCID 671329302-(3-Hexyl-phenyl)-4,5-diiodo-1-methyl-1H-imidazoleHCID 178418339Butyllithium

Produkt 1

HCID 671332392-(3-Hexyl-phenyl)-5-iodo-3-methyl-3H-imidazole-4-carboxylic acidAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 7.27 g (14.7 mmol) of 2-(3-hexyl-phenyl)-4,5-diiodo-1-methyl-1H-imidazole in 150 ml of THF was cooled down to −75° C.; then, 11.95 ml (19.1 mmol) of an n-butyl lithium solution (1.6 molar in n-hexane) was added drop by drop below −70° C. 30 min later, the reaction mixture was treated with an excess of solid carbon dioxide and subsequently warmed up to RT. It was then poured into crashed ice and extracted twice with EtOAc; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 4:1) to give 2.97 g (49%) of the title compound as light red oil. MS: 411.2 ([M-H]−).

Aufarbeitung

  1. additionIt was then poured
  2. extractionextracted twice with EtOAc
  3. washthe organic phases were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-0b43dc0348244c5da7ce19c5aaf4b002
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935707B2

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