Thiophene → Methyl 5,5-dimethyl-5,6-dihydro-8-(2-thienyl)-2-naphthalenecarboxylate

Temperature

0 °C

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).

1. stirringthe resulting solution stirred for 30 minutes
2. additionThis solution was added to a second flask
3. temperaturethe resulting solution was heated to 50° C. for 3 h
4. temperatureUpon cooling to room temperature the reaction
5. customwas quenched by the addition of saturated aqueous NH4Cl
6. extractionExtraction with EtOAc
7. washby washing of the combined organic layers with H2 0 and saturated aqueous NaCl
8. dry with materialdrying over MgSO4
9. concentrationThe dry solution was concentrated under reduced pressure

ORD record

ord-a1a217251deb4441871a62298b7b4aed

Source dataset

uspto-grants-1998_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05747542