2-Benzyl-1,3,4-oxadiazole → (5-Benzyl-[1,3,4]oxadiazol-2-yl)-[5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-methanol

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Reaktionsgleichung

[CH2:1]([C:8]1[O:9][CH:10]=[N:11][N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.CCOCC.[Mg+2].[Br-].[Br-].[Br:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[O:37][N:36]=[C:35]([CH3:38])[C:34]=2[CH:39]=[O:40])=[CH:29][CH:28]=1>C1COCC1>[CH2:1]([C:8]1[O:9][C:10]([CH:39]([C:34]2[C:35]([CH3:38])=[N:36][O:37][C:33]=2[C:30]2[CH:31]=[CH:32][C:27]([Br:26])=[CH:28][CH:29]=2)[OH:40])=[N:11][N:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: -70 °C

Versuchsvorschrift

2-Benzyl-[1,3,4]oxadiazole (0.500 g, 3.12 mmol) was dissolved in THF and cooled to −70° C. then n-butyllithium (1.5M in THF, 2.1 mL, 3.12 mmol) was added and the reaction stirred for 1.5 hours. Magnesium bromide ethyl etherate (0.631 g, 3.43 mmol) was added and the reaction was allowed to warm to −45° C. After 45 minutes 5-(4-bromo-phenyl)-3-methyl-isoxazole-4-carbaldehyde (0.415 g, 1.56 mmol) in THF (2 mL) was added and the reaction was allowed to stir overnight. The reaction was quenched with aqueous ammonium chloride then submitted to standard workup and purification via silica gel chromatography (0-60% EtOAc in hexanes) to give the title compound.

Aufarbeitung

temperatureto warm to −45° C
stirringto stir overnight
customThe reaction was quenched with aqueous ammonium chloride
customthen submitted to standard workup and purification via silica gel chromatography (0-60% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-d38c8376584d4b5ca50b8b5589d5e357
Quelldatensatz: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08664220B2

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