反应详情

To a stirred suspension of zinc dust (0.67 g) activated with hydrochloric acid in THF (15 ml), 2-benzylthio-2-methylpropionaldehyde (1.00 g) dissolved in THF (5 ml) and dimethyl 2-bromomethylfumarate (1.28 g) dissolved in THF (5 ml) were added dropwise in the order named while refluxing under nitrogen atmosphere. The mixture was refluxed for an additional 1.5 hours and saturated aqueous ammonium chloride solution was added to it. After cooling the mixture was filtered by celite. A reaction product was extracted with ethyl acetate from the filtrate. The organic layer was washed with 1N hydrochloric acid, water and then saturated sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The oily residue was purified by silica gel column chromatography to give 0.63 g (38%) of the titled compound.

1. additionwere added dropwise in the order
2. temperaturewhile refluxing under nitrogen atmosphere
3. temperatureThe mixture was refluxed for an additional 1.5 hours
4. temperatureAfter cooling the mixture
5. filtrationwas filtered by celite
6. extractionA reaction product was extracted with ethyl acetate from the filtrate
7. washThe organic layer was washed with 1N hydrochloric acid, water
8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
9. concentrationconcentrated in vacuo
10. customThe oily residue was purified by silica gel column chromatography