反応 #7939
ord-adef68c798704d7e9c50dde96c01cffe
反応方程式
反応物
反応条件
後処理
- 1その他was purged with nitrogen
- 2その他The resulting mixture was purged with nitrogen
- 3温度After cooling
- 4その他the solvent was evaporated under vacuum
- 5洗浄The residue in EtOAc (10 mL) was washed with water (2×5 mL) and brine (5 ml)
- 6乾燥dried over MgSO4
- 7ろ過filtered
- 8その他evaporated under vacuum to a gum (194 mg)
- 9その他The crude product was purified by preparative layer chromatography (PLC) on two 0.1×20×20 cm silica gel GF plates
- 10洗浄The major UV visible band at Rf 0.15-0.25 was eluted with EtOAc
- 11その他the solvent evaporated under vacuum
実験手順
A mixture of 9a-butyl-7-methoxy-4-[4-(trifluoromethane-sulfonyloxy)-phenyl]-1,2,9,9a-tetrahydro-3H-fluoren-3-one (98.9 mg, 0.2 mmol), methyl (E)-3-tributylstannyl-acrylate (112.5 mg, 0.3 mmol) and lithium chloride (25.4 mg, 0.6 mmol) in anhydrous dimethylformamide (1.0 mL) was purged with nitrogen and treated with bis(triphenylphosphine)palladium(II) chloride (7.0 mg, 0.01 mmol). The resulting mixture was purged with nitrogen then stirred under a nitrogen atmosphere with heating in an oil bath at 90° C. for 60 minutes. After cooling, the solvent was evaporated under vacuum. The residue in EtOAc (10 mL) was washed with water (2×5 mL) and brine (5 ml), dried over MgSO4, filtered, and evaporated under vacuum to a gum (194 mg). The crude product was purified by preparative layer chromatography (PLC) on two 0.1×20×20 cm silica gel GF plates, developing with 4:1-hexanes-EtOAc. The major UV visible band at Rf 0.15-0.25 was eluted with EtOAc and the solvent evaporated under vacuum to afford methyl (2E)-3-[4-(9a-butyl-7-methoxy-3-oxo-2,3,9,9a-tetrahydro-1H-fluoren-4-yl)phenyl]-2-propenoate (83 mg) as a pale yellow solid. NMR showed approximately 7-8% of a Bu3SnX impurity.