Dimethyl Sulfoxide → HCID 58954784, compound

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).

1. stirringthe mixture was stirred for 30 mins at −20° C
2. stirringthe resulting suspension was stirred for 1 hr at a temperature in the range of from −20° C. to 20° C.
3. washwashed with water and brine
4. extractionThe combined washings were back-extracted with Et2O once
5. washwashed with brine
6. dry with materialThe combined extracts were dried over Na2SO4
7. customevaporated
8. customto give an oily residue
9. customIt was purified by Combiflash (120 g silica gel)
10. washeluting with 5:95

ORD record

ord-670a93f677aa4a30b9d049443107a8dd

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822510B2