Dimethyl Sulfoxide → HCID 58954784, compound

Participants

Reaction Steps

To a solution of oxalyl chloride (0.851 mL, 9.72 mmol) in 15 ml of CH2Cl2 at −20° C. was added DMSO (0.690 mL, 9.72 mmol) dropwise, and the mixture was stirred for mins. Then a solution of (1-(3-fluorophenyl)cyclohexyl)methanol (675 mg, 3.24 mmol) in 5 mL of CH2Cl2 was added dropwise and the mixture was stirred for 30 mins at −20° C. Next, triethylamine was added (1.807 mL, 12.96 mmol) dropwise, and the resulting suspension was stirred for 1 hr at a temperature in the range of from −20° C. to 20° C. and then for 1.5 hrs at room temperature. It was diluted with Et2O and washed with water and brine. The combined washings were back-extracted with Et2O once and washed with brine. The combined extracts were dried over Na2SO4 and evaporated to give an oily residue. It was purified by Combiflash (120 g silica gel) eluting with 5:95 followed by 2:8 EtOAc-hexane to give 1-(3-fluorophenyl)cyclohexanecarbaldehyde (470 mg, 70.3% yield) as an oil. 1H NMR (400 MHz, CCl3D) δ ppm 9.37 (1H, s), 7.33 (1H, td, J=8.02, 6.15 Hz), 7.07-7.11 (1H, m), 7.04 (1H, dt, J=10.77, 2.20 Hz), 6.94-7.00 (1H, m), 2.28 (2H, dd, J=13.51, 4.94 Hz), 1.83 (2H, ddd, J=13.62, 10.55, 3.30 Hz), 1.29-1.72 (6H, m).

Provenance & Evidence