反応 #1487
ord-d9c61c395e2c4475a549c72777a848f0
反応方程式
反応物
試薬
反応条件
後処理
- 1workup.STIRRINGthe resulting solution stirred for 30 minutes
- 2workup.ADDITIONThis solution was added to a second flask
- 3温度the resulting solution was heated to 50° C. for 3 h
- 4温度Upon cooling to room temperature the reaction
- 5その他was quenched by the addition of saturated aqueous NH4Cl
- 6抽出Extraction with EtOAc
- 7洗浄by washing of the combined organic layers with H2O and saturated aqueous NaCl
- 8乾燥drying over MgSO4
- 9濃縮The dry solution was concentrated under reduced pressure
実験手順
(Compound E5) To a solution of 329.0 mg (3.93 mmol) of thiophene in 2.0 mL THF at 0° C. was added 251.8 mg (3.93 mmol, 1.56 mL of 2.5M solution in hexanes) of n-butyllithium. After stirring for 3 h at 0° C., a solution of 845.0 mg (6.28 mmol) of ZnCl2 in 5.0 mL THF was added and the resulting solution stirred for 30 minutes. This solution was added to a second flask containing 570.0 mg (1.57 mmol) of methyl 5,5-dimethyl-5,6-dihydro-8-(trifluoromethylsulfonyl)oxy-naphthalene-2-carboxylate (Compound E4) and 76.0 mg (0.063 mmol) of tetrakis(triphenyphosphine)palladium(0) in 4.0 mL THF, and the resulting solution was heated to 50° C. for 3 h. Upon cooling to room temperature the reaction was quenched by the addition of saturated aqueous NH4Cl. Extraction with EtOAc was followed by washing of the combined organic layers with H2O and saturated aqueous NaCl, and drying over MgSO4. The dry solution was concentrated under reduced pressure and the title compound was isolated from the residue as a yellow oil by column chromatography (5-10% EtOAc/hexanes).