反応 #52865

反応方程式

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

溶媒

THF

THF

THF

反応条件

後処理

1. 1
   workup.STIRRINGthe resulting solution stirred for 30 minutes
2. 2
   workup.ADDITIONThis solution was added to a second flask
3. 3
   温度the resulting solution was heated to 50° C. for 3 h
4. 4
   温度Upon cooling to room temperature the reaction
5. 5
   その他was quenched by the addition of saturated aqueous NH4Cl
6. 6
   抽出Extraction with EtOAc
7. 7
   洗浄by washing of the combined organic layers with H2O and saturated aqueous NaCl
8. 8
   乾燥drying over MgSO4
9. 9
   濃縮The dry solution was concentrated under reduced pressure

実験手順

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).

出典