Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ethyl bromoacetate | HCID 7748 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 131729807 | HCID 131729807 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 131729808 | HCID 131729808 | 95.8% |
Reaction Steps
Ethyl[2-(5-methylfuran-2-yl)ethyl]carbamate (0.60 g) prepared in the step 3 was dissolved in 6 mL of DMF, 0.15 g of 60% sodium hydride was slowly added thereto with stirring and ice-cooling and the mixture was stirred at room temperature for 1 hour more. Ethyl bromoacetate (0.40 g) was slowly dropped into the reaction solution under cooling with ice and the mixture was made back to room temperature followed by stirring overnight. The reaction solution was poured over 20 mL of water followed by extracting with diethyl ether. The organic layer was washed with water and a saturated solution of sodium chloride successively and dried over anhydrous magnesium sulfate and the solvent was evaporated therefrom in vacuo. The residue was purified by silica gel column chromatography to give 0.65 g of the objective compound as pale yellow liquid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08217031B2 |
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| Source dataset | uspto-grants-2012_07 |
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| ORD ID | ord-5e6b3dd4f4f2486c876c77c5808fcea9 |
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| Source note | uspto-grants-2012_07 |
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