Reaction equation
Br[C:2]([F:9])([F:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[F:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23](=[O:25])[CH3:24])=[CH:19][CH:18]=2)=[N:15][CH:16]=1.[I-].[I-].[Sm+2]>O1CCCC1>[F:8][C:2]([F:9])([C:23]([C:20]1[CH:19]=[CH:18][C:17]([C:14]2[CH:13]=[CH:12][C:11]([F:10])=[CH:16][N:15]=2)=[CH:22][CH:21]=1)([OH:25])[CH3:24])[C:3]([O:5][CH2:6][CH3:7])=[O:4]Participants
Procedure
A solution of ethyl bromo(difluoro)acetate (0.53 mL, 4.1 mmol) and 1-[4-(5-fluoropyridin-2-yl)phenyl]ethanone (800 mg, 3.7 mmol) in tetrahydrofuran (40 mL) was added to a 0.1 M solution of samarium diiodide in tetrahydrofuran (82 mL, 8.2 mmol) at ambient temperature. After stirring at ambient temperature for 3 min, the reaction was cooled and quenched with 1N aqueous hydrochloric acid. Volatiles were removed in vacuo and the residue was partitioned between ethyl acetate and 1 N hydrochloric acid. The organic phase was washed with saturated aqueous sodium bicarbonate and brine, dried (sodium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-40% ethyl acetate/hexane afforded ethyl 2,2-difluoro-3-[4-(5-fluoropyridin-2-yl)phenyl]-3-hydroxybutanoate.
Workup
- temperaturethe reaction was cooled
- customquenched with 1N aqueous hydrochloric acid
- customVolatiles were removed in vacuo
- customthe residue was partitioned between ethyl acetate and 1 N hydrochloric acid
- washThe organic phase was washed with saturated aqueous sodium bicarbonate and brine
- dry with materialdried (sodium sulfate)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-fa34da50d3594135831c5b413bedfab8
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08193228B2
Linked notes
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