Acetone → [6-chloro-2-trifluoromethyl-7-(2,4,6-trimethyl-phenyl)-7H-imidazo[1,2-a]imidazol-3-yl]-methanol

HRID 1293090

Reaktionsgleichung

Reaktionsgleichung von HRID 1293090
C([O:3][C:4]([C:6]1[N:10]2[CH:11]=[C:12]([Cl:23])[N:13]([C:14]3[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[CH3:22])[C:9]2=[N:8][C:7]=1[C:24]([F:27])([F:26])[F:25])=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].CC(C)=O.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>O1CCCC1>[Cl:23][C:12]1[N:13]([C:14]2[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=2[CH3:22])[C:9]2[N:10]([CH:11]=1)[C:6]([CH2:4][OH:3])=[C:7]([C:24]([F:25])([F:26])[F:27])[N:8]=2

Komponenten

6

Edukt 4

HCID 180AcetoneHCID 9357Potassium Sodium TartrateHCID 207802236-Chloro-2-trifluoromethyl-7-(2,4,6-trimethyl-phenyl)-7H-imidazo[1,2-a]imidazole-3-carboxylic Acid Ethyl EsterHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 21916271[6-chloro-2-trifluoromethyl-7-(2,4,6-trimethyl-phenyl)-7H-imidazo[1,2-a]imidazol-3-yl]-methanolAusbeute 90,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 6-chloro-2-trifluoromethyl-7-(2,4,6-trimethyl-phenyl)-7H-imidazo[1,2-a]imidazole-3-carboxylic acid ethyl ester (978.3 mg, 1.904 mmol) in tetrahydrofuran (100 mL) at 0° C. was added a 1.0M solution of lithium aluminum hydride in tetrahydrofuran (5.71 mL, 5.71 mmol). The resulting solution was stirred at 0° C. for 10 min. Acetone (5 mL) was added and the solution was added via cannula to a vigorously stirred ice-cold solution of Rochelle's salt (100 mL). The product was extracted with ethyl acetate (5×50 mL) and the combined organic extracts were dried over anhydrous Na2SO4. The solvent was removed in vacuo and the crude mixture was chromatographed on short silica gel column (hexanes-ethyl acetate 4:1) to give the desired product (614.8 mg, 90%) which was pure by LC-MS. LC/MS: tR=1.25 min., MS: [M+H]=358.

Aufarbeitung

  1. extractionThe product was extracted with ethyl acetate (5×50 mL)
  2. dry with materialthe combined organic extracts were dried over anhydrous Na2SO4
  3. customThe solvent was removed in vacuo
  4. customthe crude mixture was chromatographed on short silica gel column (hexanes-ethyl acetate 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-1b3f30add0244ba1b26faa73866a9543
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07238699B2

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