Phosphorus oxychloride → HCID 86648182, compound

Temperature

0 °C

To a 100 mL pear flask was added N,N-dimethylformamide (498 μl) and dichloromethane (8.9 mL) to give a colorless solution. The solution was cooled to 0° C. and POCl3 (550 μl) was added dropwise and then the mixture was warmed to room temperature for 30 minutes. In the meantime, to a 100 mL pear shaped flask was added EXAMPLE 353C (870 mg, 5.36 mmol) in dichloromethane (8941 μl) to give a colorless solution. The Vilsmeier reagent was then taken up in a syringe and added dropwise to the 4,4-bis(fluoromethyl)cyclohexanone (870 mg) solution at room temperature. The resulting solution was stirred overnight. The reaction was poured into saturated aqueous NaHCO3 and ice, warmed to room temperature and extracted with dichloromethane (3×30 mL). The organics were combined, dried over MgSO4, filtered and concentrated by rotary evaporation. The residue was purified by regular phase flash column chromatography (Analogix (0-60% hexanes/ethyl acetate).

1. customto give a colorless solution
2. temperaturethe mixture was warmed to room temperature for 30 minutes
3. customto give a colorless solution
4. temperaturewarmed to room temperature
5. extractionextracted with dichloromethane (3×30 mL)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated by rotary evaporation
9. customThe residue was purified by regular phase flash column chromatography (Analogix (0-60% hexanes/ethyl acetate)

ORD record

ord-d9b9a2fe3032485f85f07df4b1ac0082

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08580794B2