Benzaldehyde → 3-phenyl-5-(beta-hydroxyphenethyl)-N-methyl-isoxazole-4-carboxamide

Participants

Reaction Conditions

Reaction Steps

A suspension of 75 grams (0.348 mole) of 3-phenyl-5,N-dimethyl-isoxazole-4-carboxamide in 1 liter of tetrahydrofuran is cooled to -65° C. and 478 milliliters of 1.6M n-butyllithium in hexane (0.765 mole) is added dropwise maintaining the temperature between -60° C. and -70° C. After the addition is complete, the orange suspension is stirred for 11/2 hours at -60° C. to -70° C., and then 37.2 grams (0.350 mole) of benzaldehyde in 375 milliliters tetrahydrofuran is added dropwise maintaining the temperature between -60° C. and -70° C. After addition is complete, the mixture is stirred 11/2 hours at -60° C. to -70° C. and then warmed to -30° C. and quenched by the addition of saturated ammonium chloride solution. The mixture is further diluted with tetrahydrofuran and the layers are separated. The tetrahydrofuran layer is washed twice with 50 percent brine, and once with brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The solid residue is triturated with a 50:50 mixture of ether:petroleum ether, filtered and washed with cold ether to give 3-phenyl-5-(β-hydroxyphenethyl)-N-methyl-isoxazole-4-carboxamide, m.p. 183°-184° C.

Provenance & Evidence