HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1478205Generated: November 2, 2026
Dichloromethane → (E)-Ethyl 4-methyl-5-(prop-1-en-1-yl)isoxazole-3-carboxylate
https://huagongshe.com/reaction/1478205
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Potassium trans-1-propenyltrifluoroborate | HCID 49761691 | — |
| Reactant | Ethyl 5-bromo-4-methyl-1,2-oxazole-3-carboxylate | HCID 58828802 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | (E)-Ethyl 4-methyl-5-(prop-1-en-1-yl)isoxazole-3-carboxylate | HCID 125490638 | — |
Reaction Steps
A suspension of potassium trans-1-propenyltrifluoroborate (9.86 g, 66.7 mmol), PdCl2(dppf).DCM adduct (907 mg, 1.11 mmol), ethyl 5-bromo-4-methylisoxazole-3-carboxylate (Intermediate A) (13 g) and triethylamine (7.7 mL) in EtOH (250 mL) was degassed under vacuum and back-filled with nitrogen before heating at 90° C. for 18 h. After cooling to room temperature, the reaction was partitioned between EtOAc and brine, separated, dried over MgSO4 and concentrated under reduced pressure. The crude material was adsorbed onto silica and purification by chromatography eluting with 5-10% EtOAc in iso-hexane afforded the title compound;
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09403810B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-c9d8be99ee37425882051e9378c7c96a |
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| Source note | uspto-grants-2016_08 |
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