Water → 1-Chloro-2-(2,4-difluorophenyl)butane-2,3-diol
Reaction equation
[Cl:1][CH2:2][C:3]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[F:22])([OH:14])[CH:4]([O:6][Si](C(C)(C)C)(C)C)[CH3:5].[F-].[K+].O.C(OCC)(=O)C>CO>[Cl:1][CH2:2][C:3]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[F:22])([OH:14])[CH:4]([OH:6])[CH3:5]Participants
Procedure
To a solution of 0.27 g (0.77 mmol) of 1-chloro-2-(2,4-difluorophenyl)-3-(tert-butyldimethylsilyloxy)butan-2-ol ((2S,3R)/(2R,3R)=91/9) in 3 mL of methanol was added 0.06 g (0.94 mmol) of potassium fluoride, and reaction was performed for 10 hours and then at 50° C. for another 25 hours. Next, 5 mL of water was added to stop the reaction, and extraction was performed with 10 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. The resulting crude product was quantitatively analyzed by HPLC (under the same HPLC measurement conditions as those in Example 6). Thereby, the title compound was obtained in a yield of 17% ((2S,3R)/(2R,3R)=95/5).
Workup
- waitat 50° C. for another 25 hours
- customthe reaction, and extraction
- dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customto obtain a crude product as a colorless oil
Sources & evidence
- ORD record
- ord-a125feee18d0457d957eda867789655c
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07582781B2
Reaction notes
Loading…