Tetrahydrofuran → HCID 18424484, compound

Into a reactor were introduced 10.0 g (40.6 mmol) of cerium chloride and 80 mL of THF under a nitrogen atmosphere. This mixture was stirred at room temperature for 20 hours and then cooled to 0° C. Thereto was added dropwise 25.1 mL (24.3 mmol; 0.97 M THF solution) of ethylmagnesium chloride over 30 minutes. Subsequently, a solution prepared by mixing 3.54 g (16.2 mmol) of 4,4′-difluorobenzophenone with 20 mL of THF was added dropwise thereto over 40 minutes, and this mixture was stirred for 1 hour. To the resultant reaction mixture was added 10% aqueous acetic acid solution. Thereafter, the mixture was extracted with ethyl acetate, and the resultant organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution, subsequently dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure. The concentrate was purified by column chromatography to obtain 3.12 g (78%) of the target compound as a light-yellow oily substance.

1. temperaturecooled to 0° C
2. customSubsequently, a solution prepared
3. additionwas added dropwise
4. waitover 40 minutes
5. stirringthis mixture was stirred for 1 hour
6. customTo the resultant reaction mixture
7. extractionThereafter, the mixture was extracted with ethyl acetate
8. washthe resultant organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution
9. dry with materialsubsequently dried with anhydrous magnesium sulfate
10. concentrationconcentrated under reduced pressure
11. customThe concentrate was purified by column chromatography

ORD record

ord-93e2bd2b9b1a43b1acf030c7ad47e4c8

Source dataset

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06455720B1