反应详情

To a solution of 2-trimethylsilyl-ethanesulfonic acid pyridin-3-ylmethyleneamide (665 mg) in toluene (4.5 mL) was added Danishefsky's diene (0.46 mL, 2.4 mmol) under Ar atmosphere. The mixture was heated at reflux for 90 minutes. The toluene was removed in vacuo and the residue was dissolved in dichloromethane (ca. 10 mL) and treated with 2N HCl (ca. 10 mL) for 5 minutes. 10% Aqueous sodium bicarbonate was added carefully to adjust to pH 8. The phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic extracts were dried (Na2SO4), filtered and evaporated to dryness under reduced pressure. Purification of the residue by flash chromatography (gradient hexane/ethyl acetate) gave 1-(2-trimethylsilyl-ethanesulfonyl)-2,3-dihydro-1H-[2,3′]bipyridinyl-4-one (322 mg, 40% overall).

1. temperatureThe mixture was heated
2. temperatureat reflux for 90 minutes
3. customThe toluene was removed in vacuo
4. dissolutionthe residue was dissolved in dichloromethane (ca. 10 mL)
5. additiontreated with 2N HCl (ca. 10 mL) for 5 minutes
6. addition10% Aqueous sodium bicarbonate was added carefully
7. customThe phases were separated
8. extractionthe aqueous phase was extracted with dichloromethane
9. dry with materialThe combined organic extracts were dried (Na2SO4)
10. filtrationfiltered
11. customevaporated to dryness under reduced pressure
12. customPurification of the residue by flash chromatography (gradient hexane/ethyl acetate)