Dichloromethane → Bicyclo(2.2.1)hept-5-en-2-ol, 2-acetate

Participants

Reaction Steps

To a solution of bicyclo[2.2.1]hept-5-en-2-ol (25 g) in 200 mL of anhydrous, dichloromethane is added triethylamine (30 mL) and 4-N,N-dimethylaminopyridine (30 mg). With stirring at room temperature and under an inert atmosphere, of acetic anhydride (35 mL) was added neat and dropwise to the above reaction mixture while maintaining the reaction at room temperature over 1.5 h. Upon complete addition of the anhydride the reaction is left for 3 h, the solvents were stripped and the crude mixture was purified by silica gel chromatography eluting with 25% ethyl acetate/hexanes to afford the title compound in a quantitative yield. 1H NMR (CDCl3, 400 MHz) δ 6.21 (m, 1H), 5.83 (m, 1H), 5.18 (m, 1H), 3.12 (d, 1H), 2.72 (d, 1H), 2.16 (s, 3H), 2.00 (m, 1H), 1.35 (m, 1H), 1.21 (m, 1H), 0.83 (m, 1H), APCl MS m/z 153.2 (M+H)+.

Provenance & Evidence