Water → 1-Chloro-2-(2,4-difluorophenyl)butane-2,3-diol
Reaction equation
[Cl:1][CH2:2][C:3](=[O:11])[C@H:4]([O:6][Si](C)(C)C)[CH3:5].[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[Mg]Br.[Cl-].[NH4+].O>C1COCC1>[Cl:1][CH2:2][C:3]([C:16]1[CH:15]=[CH:14][C:13]([F:12])=[CH:18][C:17]=1[F:19])([OH:11])[CH:4]([OH:6])[CH3:5]Participants
Procedure
A solution of 0.7 g (3.6 mmol) of (R)-1-chloro-3-(trimethylsilyloxy)butan-2-one in 5 mL of THF was cooled to 0° C., 5.4 mL (3.8 mmol) of a 0.7 M solution of 2,4-difluorophenylmagnesium bromide prepared by the same method as that in Example 3 was added dropwise thereto over a period of 10 minutes. After the completion of the dropwise addition, stirring was continued for another 5 hours, and 10 mL of a saturated aqueous solution of ammonium chloride was added to stop the reaction. Furthermore, 10 mL of water was added, and extraction was performed with ethyl acetate (20 mL×2). After drying over anhydrous sodium sulfate, concentration was performed under reduced pressure to obtain 1-chloro-2-(2,4-difluorophenyl)butane-2,3-diol. A quantitative analysis was performed by HPLC (under the same HPLC measurement conditions as those in Example 6). As a result, the yield was determined to be 87% ((2S,3R)/(2R,3R)=41/59).
Workup
- additionwas added dropwise
- additionAfter the completion of the dropwise addition
- waitwas continued for another 5 hours
- customthe reaction
- extractionextraction
- dry with materialAfter drying over anhydrous sodium sulfate, concentration
Sources & evidence
- ORD record
- ord-a60c73777d054bffbe5b7debb14e95ad
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07582781B2
Reaction notes
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