Dimethylformamide → HCID 58604055, compound

Participants

Reaction Conditions

Reaction Steps

NaH (0.31 g of a 60% dispersion in mineral oil, 7.6 mmol) was added to an ice-cold solution of 2-ethyl-6-methoxy-3,4-dihydro-1(2H)-naphthalenone (1.48 g, 7.2 mmol) in anhydrous DMF (14.4 mL). The mixture was purged with N2 and stirred at 0-5° C. for 45 minutes. Allyl iodide (1.0 mL, 10.9 mmol) was added and, after a few minutes, the cooling bath was removed. After stirring overnight at room temperature, the mixture was partitioned between EtOAc and water, and the aqueous phase was back-extracted several times with EtOAc. 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 to afford 2-allyl-2-ethyl-6-methoxy-3,4-dihydro-1(2H)-naphthalenone as an oil.

Provenance & Evidence