Acetophenone → (E)-3-Dimethylamino-1-phenyl-propenone
Reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C(O[CH:13](OCC)[N:14]([CH3:16])[CH3:15])C>CN(C=O)C>[CH3:13][N:14]([CH3:16])/[CH:15]=[CH:2]/[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
Acetophenone (1.18 mL) and N,N-dimethylformamide diethyl acetal (1.71 mL) were dissolved in DMF (4 mL) and the resulting mixture was stirred at 120° C. for 20 h. The solvent was removed in vacuo and the residue was crystallized in Et2O. The mother liquors were cooled to 0° C. and precipitation occurred. The solid was filtered off and combined with the first batch to afford (E)-3-(dimethylamino)-1-phenylprop-2-en-1-one (1.02 g of yellow solid).
Workup
- customThe solvent was removed in vacuo
- customthe residue was crystallized in Et2O
- temperatureThe mother liquors were cooled to 0° C.
- customprecipitation
- filtrationThe solid was filtered off
Sources & evidence
- ORD record
- ord-46616c494bf94eddba85c14610ebe14e
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09266876B2
Reaction notes
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