تفاعل #1376504

معادلة التفاعل

thiophene

n-butyllithium

methyl 5,5-dimethyl-5,6-dihydro-8-(trifluoromethylsulfonyl)oxy-naphthalene-2-carboxylate

Compound E4

methyl 5,5-dimethyl-5,6-dihydro-8-(trifluoromethylsulfonyl)oxy-naphthalene-2-carboxylate

→

title compound

Methyl 5,5-dimethyl-5,6-dihydro-8-(2-thienyl)-naphthalene-2-carboxylate

المذيبات

THF

THF

THF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe resulting solution stirred for 30 minutes
2. 2
   workup.ADDITIONThis solution was added to a second flask
3. 3
   درجة الحرارةthe resulting solution was heated to 50° C. for 3 h
4. 4
   درجة الحرارةUpon cooling to room temperature the reaction
5. 5
   أخرىwas quenched by the addition of saturated aqueous NH4Cl
6. 6
   استخلاصExtraction with EtOAc
7. 7
   غسيلby washing of the combined organic layers with H2 0 and saturated aqueous NaCl
8. 8
   تجفيفdrying over MgSO4
9. 9
   تركيزThe 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 2.5M 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(O) 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 H2 0 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).

المصدر