(4-Benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-methanol → 4-Benzyloxy-6-fluoro-3-methyl-naphthalene-2-carbaldehyde

Participants

Reaction Steps

To a solution of (4-benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-methanol (180 mg, 0.6 mmol) in dichloromethane (10 mL) was added pyridinium chlorochromate (260 mg, 1.2 mmol) in portions. After being stirred at room temperature for 3 hours, the resulting dark mixture was diluted with diethyl ether, and stirred at room temperature for 10 minutes. The mixture was filtered through a short silica gel column. The filtrate was concentrated in vacuo to give 4-benzyloxy-6-fluoro-3-methyl-naphthalene-2-carbaldehyde (165 mg, 93%) as a white solid, which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ ppm 10.31 (s, 1H), 8.16 (s, 1H), 8.00 (dd, J=8.84, 5.56 Hz, 1H), 7.73 (dd, J=10.48, 2.40 Hz, 1H), 7.55 (d, J=6.82 Hz, 2H), 7.39-7.49 (m, 2H), 7.32 (td, J=8.65, 2.65 Hz, 1H), 4.99 (s, 2H), 2.75 (s, 3H).

Provenance & Evidence