反应详情

A solution of 60% NaH (2.27 g, 56.75 mmoles) in tetrahydrofuran (15 mL) was cooled to 0° C. and to the solution cis-2-butene-1,4-diol (5.0 g, 56.75 mmoles) in tetrahydrofuran (10 mL) was added. The reaction was stirred at room temperature for thirty minutes and tert-butyl-chloro-dimethyl-silane (8.56 g, 56.75 mmoles) in tetrahydrofuran (15 mL) was added and stirred for another two hours. The reaction was quenched with 10% NH4Cl and extracted with ethyl acetate. The organic layer was washed with brine (30 mL), dried with MgSO4, filtered, and evaporated in vacuo. The crude oil was purified by flash column chromatography (hexanes:ethyl acetate 100:0 to 50:50). The resulting product was dissolved in dichloromethane (25 mL) and pyridine (3.95 g, 50.6 mmoles) and isobutyryl chloride (2.68 g, 25.3 mmoles) were added. Then, the solution was stirred at room temperature for twelve hours. The reaction was quenched with water and extracted with dichloromethane. The organic layer was washed with water (50 mL), dried with MgSO4, filtered and evaporated in vacuo. The solvent was evaporated in vacuo and the product was purified by flash column chromatography (hexanes:ethyl acetate 100:0 to 70:30) to provide the title compound as a colorless oil.

1. additionwas added
2. stirringstirred for another two hours
3. customThe reaction was quenched with 10% NH4Cl
4. extractionextracted with ethyl acetate
5. washThe organic layer was washed with brine (30 mL)
6. dry with materialdried with MgSO4
7. filtrationfiltered
8. customevaporated in vacuo
9. customThe crude oil was purified by flash column chromatography (hexanes:ethyl acetate 100:0 to 50:50)
10. dissolutionThe resulting product was dissolved in dichloromethane (25 mL)
11. stirringThen, the solution was stirred at room temperature for twelve hours
12. customThe reaction was quenched with water
13. extractionextracted with dichloromethane
14. washThe organic layer was washed with water (50 mL)
15. dry with materialdried with MgSO4
16. filtrationfiltered
17. customevaporated in vacuo
18. customThe solvent was evaporated in vacuo
19. customthe product was purified by flash column chromatography (hexanes:ethyl acetate 100:0 to 70:30)