Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | 2-Propenoic acid, 2-(bromomethyl)-, methyl ester | HCID 521093 | — |
| Reactant | 3-(4-Methoxyphenyl)propanal | HCID 11126607 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 9964662 | HCID 9964662 | 70% |
Reaction Steps
To a suspension formed from metallic tin (730 mg, 6.15 mmoles), diethyl ether (12.5 ml) and water (3.1 ml) were added 1.10 g (6.15 mmoles) of methyl 2-bromomethyl-2-propenoate and 1.11 g (6.77 mmoles) of 3-(4-methoxyphenyl) propanal, with catalytic quantities of acetic acid. The mixture was kept warm at 50° C. with stirring for 9 hours. At the end of this time it was poured into water (200 ml) and an extraction was performed with diethyl ether (3×100 ml). The result was dried over anhydrous sodium sulphate and vacuum concentrated, giving an oil 780 mg (70% yield) of 5-[2-(4-methoxyphenyl)-ethyl]-3-metylene-dihydrofuran-2-one [(I), R═CH3; R1═H].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06818780B2 |
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| Source dataset | uspto-grants-2004_11 |
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| ORD ID | ord-b056b5f8001d457baf7324a76635d931 |
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| Source note | uspto-grants-2004_11 |
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