Butyl iodide → HCID 58604054, compound

Participants

Reaction Steps

Ethyl 5-chloro-7-fluoro-6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate (651 mg, 2.17 mmol) was dissolved in dimethylformamide (DMF, 2.2 mL) with gentle heating. After cooling to room temperature, sodium hydride (160 mg, 61% dispersion in mineral oil, 4.0 mmol) was added to give a black solution which was placed under N2. Iodobutane (1.15 mL, 10 mmol) was added and the reaction stirred at room temperature for 19 hours. The reaction mixture was then partitioned between EtOAc/H2O and the organic portion was washed with brine, dried over MgSO4, filtered and evaporated under vacuum. The crude product was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 40S (4×7.5 cm) silica gel column, eluting with 1000 mL of 2% EtOAc in hexane. The product-containing fractions were concentrated to give ethyl 2-butyl-5-chloro-7-fluoro-6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate.

Provenance & Evidence