反应详情

温度

-30 °C

A suspension of 75 g. (0.348 mole) of 3-phenyl-5,N-dimethyl-isoxazole-4-carboxamide and 1 liter of tetrahydrofuran is cooled to -65° C. and 478 ml. of 1.6 M n-butyllithium in hexane (0.765 mole) is added dropwise maintaining the temperature between -60° and -70° C. After the addition is complete, the orange suspension is stirred for 11/2 hours at -60° to -70° C., and then 37.2 g. (0.350 mole) of benzaldehyde in 375 ml. tetrahydrofuran is added dropwise maintaining the temperature between -60° and -70° C. After addition is complete the mixture is stirred 11/2 hours at -60° 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% 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.

1. additionA suspension of 75 g
2. temperaturemaintaining the temperature between -60° and -70° C
3. additionAfter the addition
4. temperaturemaintaining the temperature between -60° and -70° C
5. additionAfter addition
6. stirringis stirred 11/2 hours at -60° to -70° C.
7. customquenched by the addition of saturated ammonium chloride solution
8. additionThe mixture is further diluted with tetrahydrofuran
9. customthe layers are separated
10. washThe tetrahydrofuran layer is washed twice with 50% brine
11. dry with materialonce with brine, dried over anhydrous magnesium sulfate
12. filtrationfiltered
13. customevaporated in vacuo
14. customThe solid residue is triturated with a 50:50 mixture of ether
15. filtrationpetroleum ether, filtered
16. washwashed with cold ether