Boron trifluoride etherate → 2-Acetyl-7-methoxy-3,4-dihydro-2H-naphthalen-1-one

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Reaction Steps

Boron trifluoride etherate (0.53 mL) was added dropwise to a stirred mixture of 7-methoxytetralone (176 mg, 1 mmol) in acetic anhydride (1.8 mL). The reaction was stirred at room temperature for 2 hours, then poured into ice-water and stirred for 1 hour. The mixture was extracted with ether, and the ether extracts were evaporated. The residue was diluted with methanol (12 mL) and saturated sodium acetate (8 mL) and stirred at reflux for 4 hours. After cooling to room temperature, the solution was extracted with dichloromethane. The organic extracts were washed with brine, dried over MgSO4, and concentrated. SiO2 chromatography with 5-20% ethyl acetate/hexanes gave 72.5 mg of the desired product. LC-MS (C13H14O3 calculated 218) m/z 217 (M−H).

Provenance & Evidence