Boron trifluoride etherate → 1-Hydroxy-4-methoxy-1-(3-methylbutyl)naphthalen-2(1h)-one

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Reaction Conditions

Reaction Steps

To a solution of Example 2D (0.43g, 1.7 mmol) in methanol (2 mL) heated at 60° C. was added boron trifluoride diethyl etherate (0.135 mL, 1.0 mmol). The reaction solution was stirred at 60° C. for 5 h. The solution was quenched with saturated NH4Cl and extracted with ethyl acetate. The organic extract was concentrated in vacuo. Column chromatography on silica (2.5% methanol/dichloromethane) afforded the title compound as a white solid (0.17 g, 37.4%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.70 (dd, J=6.43, 2.39 Hz, 6H), 0.74-0.88 (m, 1H), 0.88-1.06 (m, 1H), 1.16-1.38 (m, 1H), 1.51-1.88 (m, 2H), 3.93 (s, 3H), 5.56 (s, 1H), 5.64 (s, 1H), 7.39 (t, J=7.54 Hz, 1H), 7.52 (t, J=7.54 Hz, 1H), 7.62 (d, 1H), 7.73 (d, J=7.72 Hz, 1H); MS m/z 260.9 (M+H)+.

Provenance & Evidence