Cesium fluoride → HCID 67122548, compound
Reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]#[C:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1.[F-:14].[Cs+].F.[K]>CN(C)C=O.O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:13])/[CH:4]=[C:5](/[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)\[F:14]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
To a solution of (4-chloro-phenyl)-propynoic acid methyl ester (5.36 g) in dimethylformamide (60 ml) was added cesium fluoride (11.4 g) and potassium hydrogen fluoride (2.73 g) in water (5.4 ml) and the mixture was stirred at 80° C. for 8 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (50 ml), the organic phase washed with water (3×50 ml) and brine (3×20 ml), dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (SiO2, ethyl acetate:cyclohexan 1:9) to give 1.06 g of the desired product (20%) which was characterized by its mass and NMR spectra.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- washthe organic phase washed with water (3×50 ml) and brine (3×20 ml)
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by column chromatography (SiO2, ethyl acetate:cyclohexan 1:9)
Sources & evidence
- ORD record
- ord-9491661fbd6c44d0ab2bbcb1a8734e9a
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09174987B2
Reaction notes
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