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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence