Tetrahydrofuran → Dimethyl (3,3-dimethyl-2-oxo-4-phenylbutyl)phosphonate

참여 물질

반응 단계

To a solution of 63 g. of dimethyl methylphosphonate in 600 ml. of tetrahydrofuran under nitrogen atmosphere at -75° C. is added with stirring 312 ml. of 1.6 M n-butyllithium in hexane. The condition is regulated so as to maintain a reaction temperature below -55° C. Ten minutes after the addition, 48.2 g. of the reaction product of step B above (2,2-dimethyl-3-phenylpropionyl chloride) in 15 ml. of tetrahydrofuran is added dropswise. The dropwise addition is regulated so as to maintain a reaction temperature below -60° C. The mixture is stirred at -75° C. for 2 hr. and at ambient temperature overnight. Acetic acid (20 ml.) is added and the tetrahydrofuran is removed by distillation. The residue is shaken with diethyl ether-methylene chloride (3:1, by volume) and dilute sodium bicarbonate solution. The organic layer is washed with saturated saline and then dried and concentrated. The residue is recrystallized in diethyl ether to give 54 g. of the title compound of this preparation. Melting point 49°-51° C.

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