Dimethylformamide dimethyl acetal → Ethyl 3-(dimethylamino)-2-(4-hexylphenyl)acrylate
Reaction equation
[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].CO[CH:21](OC)[N:22]([CH3:24])[CH3:23]>CN(C)C=O.C(OCC)C>[CH3:21][N:22]([CH3:24])[CH:23]=[C:13]([C:10]1[CH:11]=[CH:12][C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:8][CH:9]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15]Participants
Conditions
- Temperature
- 60 °C
Procedure
0.50 g (2.0 mmol) of ethyl 2-(4-hexylphenyl)acetate was dissolved in 7 mL of N,N-dimethylformamide, mixed with 0.31 mL (2.3 mmol) of N,N-dimethylformamide dimethyl acetal and stirred at 60° C. for 18 hours. After the stirring, the reaction mixture was further mixed with 0.65 mL (4.9 mmol) of N,N-dimethylformamide dimethyl acetal and stirred at 60° C. for 24 hours. After completion of the reaction, the reaction mixture was diluted with diethyl ether and washed with saturated aqueous sodium hydrogen carbonate and with saturated aqueous sodium chloride successively. The organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure to give the desired product as a brown liquid.
Workup
- stirringstirred at 60° C. for 24 hours
- customAfter completion of the reaction
- washwashed with saturated aqueous sodium hydrogen carbonate and with saturated aqueous sodium chloride successively
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-394a4b5d549b4e86983c50987411648b
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658686B2
Reaction notes
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