Iodine → (6-Methylnaphthalen-2-yl)acetic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

Triethylorthoformate (1.5 ml) and 1-(6-methylnaphthalen-2-yl)ethanone (1.0 mmol) were dissolved in ethanol (4 ml). To the reaction mixture were added AgNO3 (2.1 mmol) and I2 (1.05 mmol) and the reaction mixture was heated to 80° C. for 20 hours. The reaction mixture was cooled to ambient temperature and concentrated to dryness. The residue was diluted eith EtOAc and filtered through celite. The combined organics were washed with saturated sodium bicarbonate solution and brine. The organic layer was then dried over MgSO4, filtered and concentrated to dryness. The crude residue was chromatographed on silica gel using 5% EtOAc in hexanes as the eluant to yield the title compound (50).

Provenance & Evidence