反应详情

To a solution of potassium t-butoxide (16.8 g) in t-butyl alcohol (150 ml) is added dropwise with stirring a solution of benzaldehyde (15.9 g) and succinic acid dimethyl ester (26.3 g) in t-butyl alcohol (20 ml) at room temperature, and the mixture is stirred for 30 minutes. The reaction mixture is poured into ice-water (200 ml), and the mixture is extracted with isopropyl ether. The pH value of the aqueous layer is adjusted to pH 2-3, and the mixture is extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is dissolved in methanol (75 ml), and thereto is added dropwise thionyl chloride (10.9 ml) under ice-cooling. The mixture is allowed to stand at room temperature overnight, and then evaporated to remove the solvent. To the residue is added isopropyl ether, and the mixture is washed, dried, and evaporated to remove the solvent. The resulting residue is distilled under reduced pressure to give (E)-3-methoxycarbonyl-4-phenyl-3-butenoic acid methyl ester (23.2 g) as colorless oil.

1. extractionthe mixture is extracted with isopropyl ether
2. extractionthe mixture is extracted with ethyl acetate
3. washThe ethyl acetate layer is washed
4. customdried
5. customevaporated
6. customto remove the solvent
7. dissolutionThe residue is dissolved in methanol (75 ml)
8. additionis added dropwise thionyl chloride (10.9 ml) under ice-
9. temperaturecooling
10. waitto stand at room temperature overnight
11. customevaporated
12. customto remove the solvent
13. additionTo the residue is added isopropyl ether
14. washthe mixture is washed
15. customdried
16. customevaporated
17. customto remove the solvent
18. distillationThe resulting residue is distilled under reduced pressure