Water → (2S,3R)-1-Chloro-2-(2,4-difluorophenyl)butane-2,3-diol

A solution of 0.45 g (1.28 mmol) of 1-chloro-2-(2,4-difluorophenyl)-3-(tert-butyldimethylsilyloxy)butan-2-ol ((2S,3R)/(2R,3R)=91/9) in 5 mL of THF was cooled in ice, and 1.3 mL of a 1.0 M solution of TBAF in THF was added dropwise. After the completion of the dropwise addition, reaction was performed for 1.5 hours and then at room temperature for another 11 hours. Next, 10 mL of water was added to stop the reaction, and extraction was performed with 20 mL of ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product as a colorless oil. A quantitative analysis was performed by HPLC (under the same HPLC measurement conditions as those in Example 6). Thereby, the title compound was obtained in a yield of 15% ((2S,3R)/(2R,3R)=91/9).

1. additionAfter the completion of the dropwise addition, reaction
2. waitat room temperature for another 11 hours
3. customthe reaction, and extraction
4. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
5. concentrationconcentrated under reduced pressure
6. customto obtain a crude product as a colorless oil

ORD record

ord-cb970cb2ebb447b08307a79c0d9b9aa9

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07582781B2