Réaction #1487
ord-d9c61c395e2c4475a549c72777a848f0
Équation de réaction
Réactifs
Réactifs
Conditions de réaction
Traitement
- 1workup.STIRRINGthe resulting solution stirred for 30 minutes
- 2workup.ADDITIONThis solution was added to a second flask
- 3Températurethe resulting solution was heated to 50° C. for 3 h
- 4TempératureUpon cooling to room temperature the reaction
- 5Autrewas quenched by the addition of saturated aqueous NH4Cl
- 6ExtractionExtraction with EtOAc
- 7Lavageby washing of the combined organic layers with H2O and saturated aqueous NaCl
- 8Séchagedrying over MgSO4
- 9ConcentrationThe dry solution was concentrated under reduced pressure
Mode opératoire
(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).