Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ethyl bromoacetate | HCID 7748 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1-[5-(Benzyloxy)-2-hydroxyphenyl]ethan-1-one | HCID 12870928 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 66777216 | HCID 66777216 | 17% |
Reaction Steps
To a solution (200 mL) of 1-[5-(benzyloxy)-2-hydroxyphenyl]ethanone (15.3 g) synthesized in Example A82(1) in N,N-dimethylformamide were added potassium carbonate (13.1 g) and ethyl bromoacetate (7.7 mL) at room temperature, and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The extract was concentrated under reduced pressure, the obtained residue was dissolved in N,N-dimethylformamide (100 mL) again, and 1,8-diazabicyclo[5.4.0]undec-7-ene (12.2 mL) was added to the solution. The reaction mixture was stirred at 80° C. overnight. After cooling to room temperature, water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The extract was concentrated under reduced pressure and the obtained solid was washed with ethanol-isopropyl ether to give the title object compound (3.3 g, 17%) as a colorless solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08436043B2 |
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| Source dataset | uspto-grants-2013_05 |
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| ORD ID | ord-2144a668a9d940a783044bbd8f91030f |
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| Source note | uspto-grants-2013_05 |
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