Water → HCID 68417867, compound
Reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=O.C(=O)([O-])[O-].[K+].[K+].C(OP([CH2:27][C:28]#[N:29])(=O)OCC)C.O>O1CCCC1>[C:28]([CH:27]=[CH:1][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])#[N:29]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of methyl 3-formylbenzoate (2.00 g, 12.2 mmol) in tetrahydrofuran (20 mL) were added potassium carbonate (2.02 g, 14.6 mmol), diethyl(cyanomethyl)phosphonate (2.29 mL, 14.6 mmol) and water (0.4 mL), and the mixture was stirred at 60° C. for 1 hr. To the reaction mixture was added water (50 mL), and the mixture was extracted with ethyl acetate (50 mL, 20 mL). The combined organic layer was washed with saturated brine (10 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give methyl 3-(2-cyanoethenyl)benzoate as a white solid. The obtained compound was used for the next reaction without further purification.
Workup
- extractionthe mixture was extracted with ethyl acetate (50 mL, 20 mL)
- washThe combined organic layer was washed with saturated brine (10 mL)
- dry with materialdried over anhydrous sodium sulfate
- filtrationThe insoluble material was filtered off
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-939966811a464152aa430d8be63f9eed
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08344135B2
Reaction notes
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