تفاعل #568405
ord-948d355b600c4d7dabaae2bc489c347a
معادلة التفاعل
المتفاعلات
الكواشف
ظروف التفاعل
المعالجة
- 1workup.STIRRINGthe resulting solution stirred for 30 minutes
- 2workup.ADDITIONThis solution was added to a second flask
- 3درجة الحرارةthe resulting solution was heated to 50° C. for 3 h
- 4درجة الحرارةUpon cooling to room temperature the reaction
- 5أخرىwas quenched by the addition of saturated aqueous NH4Cl
- 6استخلاصExtraction with EtOAc
- 7غسيلby washing of the combined organic layers with H2O and saturated aqueous NaCl
- 8تجفيفdrying over MgSO4
- 9تركيزThe dry solution was concentrated under reduced pressure
الإجراء التجريبي
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 2.5 M 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).