Tetrahydrofuran → Benzyl 5-(3-ethoxy-2-ethoxy-3-oxo-1-propenyl)-2-methoxybenzoate
Reaction equation
C(P([CH:7](CC)[C:8]([O:10][CH2:11][CH3:12])=[O:9])(CC)=O)C.[H-].[Na+].[CH:17]([C:19]1[CH:20]=[CH:21][C:22]([O:35][CH3:36])=[C:23]([CH:34]=1)[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])=O.[Cl-].[NH4+].[O:39]1CC[CH2:41][CH2:40]1>>[CH2:11]([O:10][C:8](=[O:9])[C:7]([O:39][CH2:40][CH3:41])=[CH:17][C:19]1[CH:20]=[CH:21][C:22]([O:35][CH3:36])=[C:23]([CH:34]=1)[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])[CH3:12]Participants
Procedure
1.5 g of ethyl 2-(diethylphosphoryl)-2-ethylacetate was dissolved in 30 ml tetrahydrofuran, and 0.26 g of 60% sodium hydride was added thereto under ice-cooling. The reaction solution was stirred for 30 minutes under ice-cooling and 1.5 g of benzyl 5-formyl-2-methoxybenzoate was added thereto, and the mixture was stirred at room temperature for 20 hours. Aqueous ammonium chloride solution was added to the reaction mixture, followed by extracting with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was subjected to silica gel column chromatography, to give 1.6 g of benzyl 5-(3-ethoxy-2-ethoxy-3-oxo-1-propenyl)-2-methoxybenzoate as an E-Z mixture from fractions eluted with hexane-ethyl acetate (4:1).
Workup
- temperatureunder ice-cooling
- temperaturecooling
- stirringthe mixture was stirred at room temperature for 20 hours
- extractionby extracting with ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated
Sources & evidence
- ORD record
- ord-59d36ff3e2b34f3c8fcb3337d6e4b321
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06884821B1
Reaction notes
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