2-Methyl-3-butyn-2-ol → HCID 11042846, compound

Participants

Reaction Steps

A mixture of 6-methoxy-2-bromonaphthalene (14.23 g, 60.0 mmol), copper (I) iodide (0.17 g, 0.90 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.63 g, 0.90 mmol), and 2-methyl-3-butyn-2-ol (8.7 mL, 90 mmol) in diethylamine (100 mL) was heated at reflux for 16 hours, cooled to room temperature and solvent evaporated. The residue was purified by flash chromatography using 15-25% ethyl acetate in hexane as an eluant. Drying at 80° C. for 20 minutes afforded 4-(6-methoxy-2-naphthyl)-2-methyl-3-butyn-2-ol as a light orange solid (14.4 g), mp: 118-119° C. 1HNMR (300 MHz, DMSO-d6): δ7.95 (s, 1H), 7.75-7.85 (m, 2H), 7.4 (dd, 1H, J=8.4 Hz and 1.5 Hz), 7.35 (d, 1H, J=2.4 Hz), 7.2 (dd, 1H, J=8.5 Hz and 1.5 Hz), 5.5 (s, 1H), 3.9 (s, 3H), and 1.5 ppm (s, 6H).

Provenance & Evidence