تفاعل #466463
ord-239f072b18914c88b8d9f29caed04e44
معادلة التفاعل
المتفاعلات
الكواشف
ظروف التفاعل
المعالجة
- 1استخلاصextracted with ethyl acetate
- 2غسيلThe organic layer was washed with saturated aqueous sodium chloride
- 3تجفيفdried with anhydrous magnesium sulfate
- 4ترشيحfiltered
- 5تركيزconcentrated at reduced pressure
- 6أخرىThe resulting oil was purified by flash column chromatography over silica gel with 4:1 ethyl acetate/hexanes
الإجراء التجريبي
To a stirred solution of benzthiazole (165 mg, 1.22 nunol) in anhydrous tetrahydrofuran (5 mL) at −78° C. was added a solution of n-butyllithium in hexanes (0.52 mL of a 2.5 M solution). After 5 minutes, a solution of zinc chloride in tetrahydrofuran (2.6 mL of a 0.50 M solution) was added and the reaction mixture was allowed to warm to ambient temperature. To the resulting solution was added 9-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-3-(trifluoromethanesulfonyloxy)-non-2-enoic acid tert-butyl ester 29-6 (400 mg, 0.81 mmol) and palladium(tetrakis)-triphenylphosphine (94 mg, 0.081 mmol) and the mixture was stirred at ambient temperature for 1 hour. The reaction mixture was then poured into saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried with anhydrous magnesium sulfate, filtered, and concentrated at reduced pressure. The resulting oil was purified by flash column chromatography over silica gel with 4:1 ethyl acetate/hexanes to give 29-7c as a colorless oil.