p-Toluenesulfonic acid → HCID 67300444, compound

Participants

Reaction Steps

A mixture of 2-[1-(benzyloxymethyl)tricyclo[3.3.1.03,7]non-3-yl]-2-methyl-1,3-dioxolane (2.6 g, 7.9 mmol), p-toluenesulfonic acid (0.3 g, 1.6 mmol), and acetone (31.6 mL) was refluxed for 4 h. The volatiles were removed under vacuum and the residue was diluted with EtOAc, washed with 10% aq. NaHCO3 and brine, dried over Na2SO4, and the solvent was evaporated under reduced pressure to obtain 1-{1-[(benzyloxy)methyl]tricyclo[3.3.1.03,7]non-3-yl}ethanone (2.1 g) as a viscous liquid in 93% yield. m/z (M+1) 285; 1H NMR (CDCl3) 300 MHz δ 7.40-7.22 (m, 5H), 4.50 (s, 2H), 3.27 (s, 2H), 2.70-2.62 (m, 1H), 2.47-2.40 (m, 1H), 2.16 (s, 2H), 2.0-1.90 (m, 2H), 1.81-1.56 (m, 7H), 1.50 (dd, J=3.0, 11.0 Hz, 1H).

Provenance & Evidence