Diisobutylaluminumhydride → {2-Methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-3-yl}-methanol

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Reaction Steps

Diisobutylaluminium hydride (DIBAL-H, 21.9 ml, 1M in toluene) is added to a solution of 2-methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-3-carboxylic acid methyl ester (5.0 g) in diethyl ether (100 ml) under nitrogen at −5° C. After 15 it at −5° C., the cold bad is removed. After 20 hours at room temperature, the reaction mixture is diluted with ethyl acetate and is quenched with a saturated solution of NaHCO3. The organic phase is separated and washed with a saturated solution of NaHCO3 and with a saturated aqueous solution of NaCl, dried over Na2SO4 and concentrated in vacuo. The crude product is purified on a semi-preparative HPLC to yield {2-methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-3-yl}-methanol (3.88 g) as a white foam. MS (HPLC/MS): 428 (MH+).

Provenance & Evidence