Benzyl 5-(4,6-dimethoxypyrimidin-2-yl)oxy-3-ethoxycarbonyl-2-methylbenzofuran-4-carboxylate → 5-(4,6-Dimethoxypyrimidin-2-yl)oxy-3-ethoxycarbonyl-2-methylbenzofuran-4-carboxylic acid
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[C:26]([C:27]([O:29]CC3C=CC=CC=3)=[O:28])=[C:16]3[C:17]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:18]([CH3:20])[O:19][C:15]3=[CH:14][CH:13]=2)[N:4]=1>C(O)C.[C].[Pd]>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([O:11][C:12]2[C:26]([C:27]([OH:29])=[O:28])=[C:16]3[C:17]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:18]([CH3:20])[O:19][C:15]3=[CH:14][CH:13]=2)[N:6]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture comprising 14.4 g of benzyl 5-(4,6-dimethoxypyrimidin-2-yl)oxy-3-ethoxycarbonyl-2-methylbenzofuran-4-carboxylate and 4.52 g of 10% palladium carbon in 100 ml of ethanol, was subjected to hydrogenation under an ordinary pressure while stirring at room temperature. After completion of the reaction, an insoluble matter was separated by filtration, and the filtrate was concentrated under reduced pressure, whereupon the precipitated crystals were washed with a solvent mixture of diethyl ether/n-hexane to obtain 10.47 g (yield: 89%) of the desired compound.
Workup
- customAfter completion of the reaction
- customan insoluble matter was separated by filtration
- concentrationthe filtrate was concentrated under reduced pressure, whereupon the precipitated crystals
- washwere washed with a solvent mixture of diethyl ether/n-hexane
Sources & evidence
- ORD record
- ord-d6d339541bde41239f4dbc25a36315a6
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05616537
Reaction notes
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