Diethyl Ether → [1-[4-(5-Methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-4-phenyl-3-pyrrolyl]methanol

HRID 349890Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 349890
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:9]=1[CH2:19][O:20][C:21]1[CH:42]=[CH:41][C:24]([CH2:25][N:26]2[CH:30]=[C:29]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:28]([C:37](OC)=[O:38])=[CH:27]2)=[CH:23][CH:22]=1.C(OCC)C.O1CCCC1>O>[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[N:10][C:9]=1[CH2:19][O:20][C:21]1[CH:42]=[CH:41][C:24]([CH2:25][N:26]2[CH:30]=[C:29]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:28]([CH2:37][OH:38])=[CH:27]2)=[CH:23][CH:22]=1

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 23024794Methyl 1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-4-phenylpyrrole-3-carboxylate

Produkt 1

HCID 69427144[1-[4-(5-Methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-4-phenyl-3-pyrrolyl]methanolAusbeute 86,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Lithium aluminium hydride (232 mg) was added to a mixture of methyl 1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-4-phenylpyrrole-3-carboxylate (2.92 g), diethyl ether (50 ml), and tetrahydrofuran (25 ml) at 0° C., and the mixture was stirred at 0° C. for 3 hours. After water was added to the reaction mixture, the precipitate was removed by filtration. The filtrate was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and then concentrated. The residue was subjected to silica gel column chromatography, and [1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-4-phenyl-3-pyrrolyl]methanol (2.37 g, yield: 86%) was obtained as a colorless amorphous substance from the fraction eluted with ethyl acetate-hexane (2:3, volume ratio).

Aufarbeitung

  1. customthe precipitate was removed by filtration
  2. extractionThe filtrate was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-41967987f3d2412986cc13caf007acde
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179823B1

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