5-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carbaldehyde → 1-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]but-3-en-1-ol

HRID 1512608Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH:14]=[O:15])=[CH:4][CH:3]=1.[CH2:16]([Mg]Br)[CH:17]=[CH2:18]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH:14]([OH:15])[CH2:18][CH:17]=[CH2:16])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

5-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carbaldehyde (0.375 g, 1.41 mmol) was dissolved in THF (3.75 mL) and cooled to 0° C. under N2 atmosphere. Allylmagnesium bromide (1 M in Et20, 1.55 mL, 1.55 mmol) was added and the reaction stirred at 0° C. for 1.5 hours. Additional allylmagnesium bromide (1 M in Et2O, 0.8 mL, 0.80 mmol) was added, and the reaction was stirred for 30 minutes at 0° C. The mixture was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were dried and concentrated and the residue was purified by silica gel chromatography (0-50% EtOAc in hexanes) to give the title compound.

Workup

stirringthe reaction was stirred for 30 minutes at 0° C
customThe mixture was quenched with saturated aqueous NH4Cl
extractionextracted with EtOAc
customThe combined organic layers were dried
concentrationconcentrated
customthe residue was purified by silica gel chromatography (0-50% EtOAc in hexanes)

Sources & evidence

ORD record: ord-5585ed723548422a9ab7c870eeb47044
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217066B2

Reaction notes

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