Nitrogen → HCID 14214131, compound

Participants

Reaction Steps

A solution of 6-methoxy-3,4-dihydro-1(2H)-naphthalenone (5.0 g, 28 mmol) in anhydrous N,N-dimethylformamide (DMF, 60 mL) was purged with N2, cooled in an ice bath, stirred, and treated with NaH (1.2 g of a 60% dispersion in mineral oil, 30 mmol). The cooling bath was removed and the mixture was stirred at room temperature for 10 minutes. The mixture was re-cooled in an ice bath, treated with iodoethane (3.35 mL, 42 mmol), and then stirred under a N2 atmosphere while gradually warming to room temperature. After stirring for 2.9 days, the mixture was diluted with EtOAc (250 mL) and washed with water (200 mL), and the aqueous phase was back-extracted with EtOAc (100 mL). The combined organics were washed with brine, dried over MgSO4, filtered, and concentrated under vacuum. The residue was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 40M (4×15 cm) silica gel column, eluting successively with 1000 mL portions of 0.2%, 1%, 2%, and 5% EtOAc in hexane. The product-containing fractions were combined and evaporated under vacuum to afford 2-ethyl-6-methoxy-3,4-dihydro-1(2H)-naphthalenone as an oil.

Provenance & Evidence