Potassium Carbonate → HCID 19603699, compound
Reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:10]([O:14][C:15]([CH2:17][O:18][C:19]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][C:20]=1[CH:21]=[O:22])=[O:16])([CH3:13])([CH3:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[C:10]([O:14][C:15]([CH2:17][O:18][C:19]1[CH:26]=[CH:25][C:24]([O:27][CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:23][C:20]=1[CH:21]=[O:22])=[O:16])([CH3:13])([CH3:11])[CH3:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
Ethyl 4-bromobutyrate (1.48 g) and 2-(tert-butoxycarbonylmethoxy)-5-hydroxybenzaldehyde (1.28 g) were dissolved in methyl ethyl ketone (20 ml). To the solution was added powdered potassium carbonate (1.05 g), and the mixture was stirred in an oil bath at 100° C. for seven hours. The reaction mixture was concentrated, diluted with water, and was extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. After concentration, the crude product was purified by a silica gel column (35 g) eluting with a mixed solvent of toluene and ethyl acetate (from 19:1 to 4:1) to give ethyl 4-(4-tert-butoxycarbonylmethoxy-3-formylphenoxy)butyrate as an oil (0.55 g)
Workup
- concentrationThe reaction mixture was concentrated
- additiondiluted with water
- extractionwas extracted with ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried over magnesium sulfate
- concentrationAfter concentration
- customthe crude product was purified by a silica gel column (35 g)
- washeluting with a mixed solvent of toluene and ethyl acetate (from 19:1 to 4:1)
Sources & evidence
- ORD record
- ord-07b9e3256be64f59885cbdec507bdc4f
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05994378
Reaction notes
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