Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Iodine | HCID 807 | — |
| Reactant | Ethyl bromoacetate | HCID 7748 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Ethyl 1-acetylcyclobutanecarboxylate | HCID 12116588 | — |
| Catalyst | Zinc | HCID 23994 | — |
| Product | HCID 86585361 | HCID 86585361 | — |
Reaction Steps
Ethyl 1-acetylcyclobutanecarboxylate (13.79 g, 81 mmol) was dissolved in tetrahydrofuran (50 ml) and zinc powder (10.59 g) and a catalytic amount of iodine were added thereto. While heating under reflux, a solution (100 ml) of ethyl bromoacetate (13.48 ml, 121 mmol) in tetrahydrofuran was added dropwise thereinto. Then, the liquid reaction mixture was heated under reflux for an additional 1 hour and allowed to cool. After adding 1 N hydrochloric acid (100 ml), the solvent was evaporated and ethyl acetate (500 ml) was added. The insoluble matter was filtered off, washed with a saturated aqueous solution of sodium chloride (300 ml) and dried over anhydrous sodium sulfate. After evaporating the solvent, the title compound was obtained in a quantitative amount as an oily substance.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06121285 |
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| Source dataset | uspto-grants-2000_09 |
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| ORD ID | ord-cf6dac2311654df3bd29c3fb9ad86f4f |
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| Source note | uspto-grants-2000_09 |
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