Hydrochloric Acid → (4-Benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-methanol

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To the slurry of lithium aluminum hydride (1.8 g, 47.5 mmol) in tetrahydrofuran (50 mL) was added a solution of 4-benzyloxy-6-fluoro-3-methyl-naphthalene-2-carboxylic acid methyl ester (10 g, 30.8 mmol) in tetrahydrofuran (50 mL) at 0° C. under a nitrogen atmosphere. After being heated at 60° C. for 2 hours, the resulting mixture was cooled to 0° C. and treated with 1 N hydrochloric acid to quench the reaction. The aqueous layer was extracted with diethyl ether (100 mL×5). The combined organic layers were dried over sodium sulfate and concentrated in vacuo to give (4-benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-methanol (8.4 g, 92%) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.84 (dd, J=5.6, 9.2 Hz, 1H), 7.70 (dd, J=2.4, 10.0 Hz, 1H), 7.69 (s, 1H), 7.40-7.50 (m, 5H), 7.24 (td, J=2.4, 8.4 Hz, 1H), 4.99 (s, 2H), 4.87 (s, 2H), 2.47 (s, 3H).

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