反应详情

温度

-70 °C

Pivalaldehyde (303.2 g, 3.41 mol, 10 eq.) and methyl {[(tert-butoxy)carbonyl]amino}-(dimethoxyphosphoryl)acetate (101.5 g, 0.341 mol, 1.0 eq.) are dissolved in THF (800 ml) and cooled to −70° C. At −70° C., TMG (78.7 g, 0.683 mmol, 6.95 ml, 2.0 eq.) is slowly added dropwise and the mixture is then stirred at −70° C. for 4 h and subsequently at RT for 4 days. The reaction mixture is concentrated and then extracted by shaking with ethyl acetate (twice 500 ml) and water, and the combined org. phases are washed with a sat. sodium chloride solution (100 ml) and dried over sodium sulfate. After concentration the crude product is chromatographed (1.5 kg of silica gel, eluent: cyclohexane/ethyl acetate 5:1). 67 g (76% of theory) of the title compound are obtained.

1. additionAt −70° C., TMG (78.7 g, 0.683 mmol, 6.95 ml, 2.0 eq.) is slowly added dropwise
2. concentrationThe reaction mixture is concentrated
3. extractionextracted
4. stirringby shaking with ethyl acetate (twice 500 ml) and water
5. washphases are washed with a sat. sodium chloride solution (100 ml)
6. dry with materialdried over sodium sulfate
7. concentrationAfter concentration the crude product
8. customis chromatographed (1.5 kg of silica gel, eluent: cyclohexane/ethyl acetate 5:1)