Isopropanol → HCID 58611868, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[1-(tert-butoxycarbonyl)cyclohexyl]benzoic acid (12) (0.219 g, 0.72 mmol) in dichloromethane (5 ml) under argon atmosphere at ice bath temperature oxalyl chloride (0.3 ml, 3.44 mmol) and a drop of dimethylformamide were added. The reaction mixture was stirred at ambient temperature for 15 minutes and at 40° C. for 1 hour, then the volatiles were evaporated and the residue was dried in vacuo. The residue (0.247 g) was dissolved in tetrahydrofuran (4 ml) and 4-dimethylaminopyridine (0.176 g, 1.43 mmol) and isopropanol (0.35 ml, 4.57 mmol) were added to the resulting solution. The mixture was stirred overnight, supplemented with benzene (50 ml), successively washed with water (30 ml), brine (20 ml), and dried (Na2SO4). The solvents were evaporated and the residue was chromatographed on silica gel with toluene-ethyl acetate (97:3) as eluent to give the title compound (0.226 g, 91%) as an oil. 1H NMR (CDCl3, HMDSO) δ: 1.01-1.87 (8H, m); 1.34 (6H, d, J=6.5 Hz); 1.34 (9H, s); 2.17-2.61 (2H, m); 5.23 (1H, sept, J=6.5 Hz); 7.46 (2H, d, J=8.8 Hz); 7.98 (2H, d, J=8.8 Hz).

Provenance & Evidence