Water → Ethyl 6-(2-isobutoxy-5-methoxyphenyl)-6-oxo-3-methylhexa-2,4-dienoate
Reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=1[C:14](=[O:22])[CH2:15]P(=O)([O-])OCC)[CH:2]([CH3:4])[CH3:3].CC(C)([O-])C.[K+].[CH3:29]/[C:30](/[CH:37]=O)=[CH:31]\[C:32]([O:34][CH2:35][CH3:36])=[O:33].O>O1CCCC1>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=1[C:14](=[O:22])[CH:15]=[CH:29][C:30]([CH3:37])=[CH:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:2]([CH3:3])[CH3:4]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
3 g (8.4 mmol) of ethyl [2-(2-isobutoxy-5-methoxyphenyl)-2-oxoethyl]-phosphonate dissolved in 20 ml of tetrahydrofuran are added dropwise to a suspension of 1.41 g (12.6 mmol) of potassium tert-butoxide in 30 ml of tetrahydrofuran, heated to 50° C. Heating is continued for 20 minutes at 50° C., the mixture is then cooled to 0° C. and 1.8 g (12.6 mmol) of ethyl 3-methyl-4-oxocrotonate dissolved in 20 ml of tetrahydrofuran are added dropwise. The reaction mixture is then stirred for 72 hours at 25° C. Water is added and the resulting mixture is extracted with ether. After drying (Na2SO4), the solvent is evaporated off and the residue is purified by flash chromatography (dichloromethane) (2.58 g of yellow oil; 89%).
Workup
- temperatureHeating
- temperaturethe mixture is then cooled to 0° C.
- additionare added dropwise
- extractionthe resulting mixture is extracted with ether
- dry with materialAfter drying (Na2SO4)
- customthe solvent is evaporated off
- customthe residue is purified by flash chromatography (dichloromethane) (2.58 g of yellow oil; 89%)
Sources & evidence
- ORD record
- ord-a324b16e61e64ab7b1a0c8ce6fe558cf
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07737176B2
Reaction notes
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