Diisobutylaluminum hydride → (5-Cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methanol

Participants

Reaction Steps

5-Cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazole-4-carboxylic acid methyl ester (0.80 g, 2.6 mmol) is dissolved in 8 mL of THF and is cooled in an ice bath. To the solution is added 1M DIBAL solution in toluene (5.66 mL) and the reaction is stirred one hour. Additional 1M DIBAL solution in toluene (5.66 mL) is added and the reaction is stirred for an additional hour. Upon completion, the reaction is quenched with methanol and acidified with aqueous HCl solution (1M). The reaction mixture is extracted with ethyl acetate and washed with brine. The organic layer is dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield the title compound (0.68 g, 93%). MS m/z: 284.0 (M++1)

Provenance & Evidence