Dichloromethane → Methyl-2-methoxy-4-[(3-oxo-2.3-dihvdrobenzo[b]furan-2-ylidene)methyl]benzoate
Reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3](=[O:10])[CH2:2]1.[C:11]([OH:14])(=[O:13])[CH3:12].O=[CH:16][C:17]1[CH:25]=[CH:24]C(O)=[C:19]([O:20][CH3:21])[CH:18]=1.[O-2].[Al+3].[O-2].[O-2].[Al+3].Cl[CH2:32]Cl>>[CH3:32][O:13][C:11](=[O:14])[C:12]1[CH:24]=[CH:25][C:17]([CH:16]=[C:2]2[O:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[C:3]2=[O:10])=[CH:18][C:19]=1[O:20][CH3:21]Participants
Procedure
2H-benzofuran-3-one 1 g and vanillin acetate 2.17 g were dissolved in dichloromethane 25 ml, aluminum oxide (manufactured by Merck Co., cat. No. 1076) 24.3 g was added, and the mixture was stirred for 1.5 hours, and aluminum oxide was filtered to obtain a reaction solution. Aluminum oxide was washed with dichloromethane 100 ml three times. This solution and the reaction solution were combined and concentrated at a temperature of 40° C. under reduced pressure. The concentrate was dissolved in methanol 40 ml, the solution was allowed to stand at room temperature for two hours. The precipitated crystals were filtered, and the resulting crystals were dried at a temperature of 60° C. for two hours under reduced pressure to obtain the desired compound 1.44 g.
Workup
- addition1076) 24.3 g was added
- filtrationaluminum oxide was filtered
- customto obtain a reaction solution
- washAluminum oxide was washed with dichloromethane 100 ml three times
- concentrationconcentrated at a temperature of 40° C. under reduced pressure
- dissolutionThe concentrate was dissolved in methanol 40 ml
- waitto stand at room temperature for two hours
- filtrationThe precipitated crystals were filtered
- customthe resulting crystals were dried at a temperature of 60° C. for two hours under reduced pressure
Sources & evidence
- ORD record
- ord-ad5f8b76fd4a41c5b3797f0797f745aa
- Source dataset
- uspto-grants-2000_11
- Patent number
- US06143779
Reaction notes
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