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

HRID 1183320Notes

Reaction equation

[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

Participants

Conditions

Temperature: -70 °C

Procedure

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.

Workup

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)

Sources & evidence

ORD record: ord-d38c8376584d4b5ca50b8b5589d5e357
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664220B2

Reaction notes

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