Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[C:17]([O:19][CH3:20])=[O:18])[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7].O[CH:22]1[C:35]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[O:29][C:28]2[C:23]1=[CH:24][CH:25]=[CH:26][CH:27]=2>C(O)C.C(O)(=O)C>[CH:24]1[C:23]2[CH:22]([CH:8]([C:6](=[O:7])[C:5]3[CH:14]=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:3]([O:2][CH3:1])[CH:4]=3)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[O:29][C:28]=2[CH:27]=[CH:26][CH:25]=1Participants
5
Procedure
To a stirred solution of ethyl 3-methoxy-4-methoxycarbonylbenzoylacetate (4.1 g, 14.6 mmol) in a mixture of ethanol (30 ml) and acetic acid (30 ml) was added portionwise 9-hydroxyxanthene (3.2 g, 16.1 mmol). After stirring for 2 weeks at room temperature, the solution was concentrated in vacuo, diluted with water and extracted with dichloromethane (2×). The combined extracts were washed with a saturated solution of sodium bicarbonate, water and dried over magnesium sulphate. Filtration and evaporation gave ethyl 2-(9H-xanthen-9-yl)-2-(3-methoxy-4-methoxycarbonyl-benzoyl)acetate as an oil.
Workup
- concentrationthe solution was concentrated in vacuo
- additiondiluted with water
- extractionextracted with dichloromethane (2×)
- washThe combined extracts were washed with a saturated solution of sodium bicarbonate, water
- dry with materialdried over magnesium sulphate
- filtrationFiltration and evaporation
Sources & evidence
- ORD record
- ord-a4de5e834eb343a7a0a041a22ba18fd8
- Source dataset
- uspto-grants-1999_04
- Patent number
- US05891899
Linked notes
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