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 (29, 578 mg, 1.26 mmol) in anhydrous THF (60 mL) was added dropwise tetrabutylammonium fluoride (1 M in THF, 1.38 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 (silical gel, 95:5 CH2Cl2/MeOH) to afford carbamate 30 (418 mg, 96%) 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