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

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)+.

1. additionwas added neat and dropwise to the above reaction mixture
2. temperaturewhile maintaining
3. customthe reaction at room temperature over 1.5 h
4. customthe crude mixture was purified by silica gel chromatography
5. washeluting with 25% ethyl acetate/hexanes

ORD record

ord-4a8a6afba1e84ff3830c63df09fe5aa2

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07456177B2