Reaction equation
C[O:2][C:3](=O)[CH:4]=[CH2:5].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]#[N:16])=[CH:10][CH:9]=1.C[O-:18].[Na+].Cl.[CH2:21]1[CH2:25][O:24][CH2:23][CH2:22]1>CO>[CH3:23][O:24][C:25]([CH:21]1[CH2:22][C:14]([C:15]#[N:16])([C:11]2[CH:12]=[CH:13][C:8]([F:7])=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]1=[O:2])=[O:18]Participants
Procedure
70 mL of methylacrylate and 50 g of 4-fluorophenylacetonitrile were dissolved in a mixture of 200 mL of THF and 50 mL of dry methanol. 150 mL of sodium methylate (30% in methanol) were added dropwise, while temperature was maintained below 40° C. The mixture was stirred at room temperature for 15 h and heated for another 4 h at 50° C. When the reaction was complete, the mixture was allowed to cool to room temperature and poured onto a cold 2N aqueous hydrochloric acid solution. The aqueous layer was extracted three times with ethyl acetate and the combined organic layer was washed with water and brine, dried over magnesium sulphate and evaporated to give 101.5 g of the desired product. Rt=1.59 min (Method 5). Detected mass: 276.2 (M+H+).
Workup
- temperaturewas maintained below 40° C
- temperatureheated for another 4 h at 50° C
- temperatureto cool to room temperature
- extractionThe aqueous layer was extracted three times with ethyl acetate
- washthe combined organic layer was washed with water and brine
- dry with materialdried over magnesium sulphate
- customevaporated
Sources & evidence
- ORD record
- ord-436b0523c98649b0bbc1c57c86e622fd
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08541449B2
Linked notes
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