Hexane → Ethyl 2-methyl-1-(2-(trimethylsilyl)ethoxymethyl)-1H-thieno[2,3-d]imidazol-5-carboxlate

HRID 1072802Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1072802
CC[O-].[Na+].[C:5]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:6][SH:7].Br[C:13]1[N:14]=[C:15]([CH3:28])[N:16]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:17]=1[CH:18]=O.CCCCCC>C(O)C>[CH3:28][C:15]1[N:16]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:26])([CH3:25])[CH3:27])[C:17]2[CH:18]=[C:6]([C:5]([O:9][CH2:10][CH3:11])=[O:8])[S:7][C:13]=2[N:14]=1

Komponenten

6

Edukt 4

HCID 8058HexaneHCID 12185Ethyl ThioglycolateHCID 2723922Sodium ethoxideHCID 220586064-Bromo-2-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)imidazole-5-carbaldehyde

Produkt 1

HCID 22387741Ethyl 2-methyl-1-(2-(trimethylsilyl)ethoxymethyl)-1H-thieno[2,3-d]imidazol-5-carboxlate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel3×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2.68 M Sodium ethylate was dissolved in ethanol (50 ml) and a solution (25 ml) of ethyl thioglycolate in ethanol was added. Thereto was added a solution (150 ml) of 4-bromo-2-methyl-1-(2-(trimethylsilyl)ethoxymethyl)imidazol-5-carboxaldehyde (3.16 g) in ethanol and the mixture was stirred at 80° C. for 2 hr. The solvent was evaporated under reduced pressure and water was added. The mixture was extracted twice with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was obtained by silica gel column chromatography (hexane/ethyl acetate=9/1). Hexane was added to the purified product and crystals were collected by filtration to give the objective compound (765 mg) as pale-brown crystals.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure and water
  2. additionwas added
  3. extractionThe mixture was extracted twice with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was obtained by silica gel column chromatography (hexane/ethyl acetate=9/1)
  8. filtrationwere collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-49ad1330475041a9a3366b77c0552228
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06911469B2

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