反应 #2307998

反应方程式

4-Isopropylbenzaldehyde

methyl{[(benzyloxy)carbonyl]amino}-(dimethoxyphosphoryl)acetate

N,N,N′,N′-tetramethylguanidine

→

title compound

Methyl (2Z)-2-{[(benzyloxy)carbonyl]amino}-3-(4-isopropylphenyl)acrylate

溶剂

tetrahydrofuran

反应条件

后处理

1. 1
   萃取The mixture is then extracted
2. 2
   workup.STIRRINGby shaking with ethyl acetate (twice 100 ml) and water
3. 3
   洗涤the combined organic phases are washed with saturated sodium chloride solution
4. 4
   干燥dried over sodium sulphate
5. 5
   浓缩After concentration
6. 6
   其他the crude product is chromatographed (Biotage 40M, cyclohexane/ethyl acetate 5/1)

实验过程

4-Isopropylbenzaldehyde (2.00 g, 13.50 mmol) and methyl{[(benzyloxy)carbonyl]amino}-(dimethoxyphosphoryl)acetate (3.58 g, 10.80 mmol, 0.8 equivalent) are dissolved in tetrahydrofuran (20 ml) and cooled to −78° C. At −78° C., N,N,N′,N′-tetramethylguanidine (27.92 g, 0.24 mol, 11.5 equivalents) is added dropwise and then stirred at −78° C. for 3 h and subsequently at room temperature 3 days. The mixture is then extracted by shaking with ethyl acetate (twice 100 ml) and water, and the combined organic phases are washed with saturated sodium chloride solution and dried over sodium sulphate. After concentration, the crude product is chromatographed (Biotage 40M, cyclohexane/ethyl acetate 5/1). 3.47 g (73% of theory) of the title compound are obtained.

来源