Hydrochloric Acid → methyl 2-bromo-3-(2-butyn-1-yl)-5-formyl-3H-imidazole-4-carboxylate

HRID 349193Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 349193
[H-].C([Al+]CC(C)C)C(C)C.[Br:11][C:12]1[N:13]([CH2:25][C:26]#[C:27][CH3:28])[C:14]([C:21]([O:23][CH3:24])=[O:22])=[C:15]([C:17](OC)=[O:18])[N:16]=1.Cl.O>O1CCCC1>[Br:11][C:12]1[N:13]([CH2:25][C:26]#[C:27][CH3:28])[C:14]([C:21]([O:23][CH3:24])=[O:22])=[C:15]([CH:17]=[O:18])[N:16]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 21947677dimethyl 2-bromo-1-(but-2-ynyl)-1H-imidazole-4,5-dicarboxylate

Produkt 1

HCID 21947682methyl 2-bromo-3-(2-butyn-1-yl)-5-formyl-3H-imidazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

43 ml of a 1 M solution of diisobutylaluminium hydride in tetrahydrofuran are added dropwise within 20 minutes to a solution of 13.5 g of dimethyl 2-bromo-1-(2-butyn-1-yl)-1H-imidazole-4,5-dicarboxylate in 220 ml of tetrahydrofuran under an argon atmosphere at −70° C. The mixture is stirred for a further four hours at −70° C., then 20 ml of a mixture of 1 M hydrochloric acid and tetrahydrofuran are added dropwise. After heating to ambient temperature approx. 200 ml of water are added and the mixture is extracted three times with 70 ml of ethyl acetate. The combined extracts are dried and evaporated down. The crude product thus obtained is purified by column chromatography through silica gel with petroleum ether/ethyl acetate (4:1->1:1) as eluant.

Aufarbeitung

  1. temperatureAfter heating to ambient temperature approx
  2. extractionthe mixture is extracted three times with 70 ml of ethyl acetate
  3. customThe combined extracts are dried
  4. customevaporated down

Quellen und Nachweise

ORD-Eintrag
ord-83503ed48b5e4d8aaa443d48407da129
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179809B2

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