Tetrabutylammonium Fluoride → Benzyl 4-(6-Hydroxynaphthalen-2-yl)but-3-ynylcarbamate

Participants

Reaction Steps

To a solution of benzyl 4-[6-(tert-butyldimethylsilyloxy)naphthalen-2-yl]but-3-ynylcarbamate (83, 2.5 g, 5.44 mmol) in anhydrous THF (25 mL) at 0° C. was added dropwise tetrabutylammonium fluoride (1 M in THF, 6.0 mL) and the mixture was stirred for 2 h at room temperature. The resulting solution was concentrated in vacuo and the residue was purified by column chromatography (silica gel, 95:5 CH2Cl2/MeOH) to afford carbamate 84 (2.0 g, 50%) as a pale yellow solid: 1H NMR (300 MHz, CDCl3) δ 7.82 (s, 1H), 7.67 (d, J=9.6 Hz, 1H), 7.58 (d, J=8.4 Hz, 1H), 7.37-7.29 (m, 6H), 7.11-7.08 (m, 2H), 5.30 (br s, 2H), 5.14 (s, 2H), 3.48 (q, J=6.3 Hz, 2H), 2.68 (t, J=6.6 Hz, 2H).

Provenance & Evidence