Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylsilane | HCID 12052 | — |
| Reactant | HCID 74020637 | HCID 74020637 | — |
| Catalyst | Chlorotris(triphenylphosphine)rhodium(I) | HCID 84599 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 23147385 | HCID 23147385 | — |
Reaction Steps
In an argon atmosphere, triethylsilane (0.15 mL, 0.94 mmol) and tris(triphenylphosphine)rhodium(I) chloride (30 mg, 0.032 mmol) were added to toluene (2.0 mL) solution of methyl 3-{5-[3-bromo-2-(methoxycarbonylmethyl)-4,6-bis(methoxymethoxy)phenyl]furan-2-yl}acrylate (89 mg, 0.18 mmol) obtained in the above, and stirred at 50° C. for 3 hours. The reaction solution was concentrated, and the residue was purified through silica chromatography (n-hexane to ethyl acetate/n-hexane=1/2) to obtain methyl 3-{5-[3-bromo-2-(methoxycarbonylmethyl)-4,6-bis(methoxymethoxy)phenyl]furan-2-yl}propanoate. Then, the resulting compound was dissolved in methanol solution (5.0 mL) of 10% hydrochloric acid, stirred at room temperature for 2 hours, and then concentrated under reduced pressure. The resulting residue was purified through preparative thin-layer chromatography (methanol/chloroform=1/9) to obtain Compound 267 (35 mg, 48%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07538241B2 |
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| Source dataset | uspto-grants-2009_05 |
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| ORD ID | ord-6c2adf5d2506423d87f744aec16bf34b |
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| Source note | uspto-grants-2009_05 |
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