반응 #52865

반응 방정식

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

용매

THF

THF

THF

반응 조건

후처리

1. 1
   workup.STIRRINGthe resulting solution stirred for 30 minutes
2. 2
   workup.ADDITIONThis solution was added to a second flask
3. 3
   온도the resulting solution was heated to 50° C. for 3 h
4. 4
   온도Upon cooling to room temperature the reaction
5. 5
   기타was quenched by the addition of saturated aqueous NH4Cl
6. 6
   추출Extraction with EtOAc
7. 7
   세척by washing of the combined organic layers with H2O and saturated aqueous NaCl
8. 8
   건조drying over MgSO4
9. 9
   농축The dry solution was concentrated under reduced pressure

실험 절차

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).

출처