反应详情

温度

60 °C

To a solution of (5-({[4-(methoxy)phenyl]methyl}oxy)-4-{[(trifluoromethyl)sulfonyl]oxy}-2-pyridinyl)methyl acetate (10 g, 23 mmol) in anhydrous toluene, (R)-(+)-2,2 bis(diphenylphosphino)-1,1-binaphthyl (312 mg, 0.4 mmol) was added. The reaction mixture was degassed before adding palladium acetate (103 mg, 0.4 mmol). Sodium 2-methyl-2-propanethiolate was added, the system degassed again and the reaction mixture was stirred at 60° C. for 3 hours, under argon atmosphere then at 70 oC for a further 18 hours. The reaction mixture was filtered and the filtrate was evaporated under vacuum. The residue was partitioned between ethyl acetate and water. The aqueous layer was extracted several times with ethyl acetate. The combined organic extracts were dried over magnesium sulfate and evaporated under vacuum. The residue was chromatographed on silica gel eluting with 20-35% ethyl acetate in hexane to afford the product as an oil (9.1 g, 100%); MS (+ve ion electrospray) m/z 376 (MH+).

1. customThe reaction mixture was degassed
2. customthe system degassed again
3. waitat 70 oC for a further 18 hours
4. filtrationThe reaction mixture was filtered
5. customthe filtrate was evaporated under vacuum
6. customThe residue was partitioned between ethyl acetate and water
7. extractionThe aqueous layer was extracted several times with ethyl acetate
8. dry with materialThe combined organic extracts were dried over magnesium sulfate
9. customevaporated under vacuum
10. customThe residue was chromatographed on silica gel eluting with 20-35% ethyl acetate in hexane