Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diethyl Ether | HCID 3283 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Triethylsilane | HCID 12052 | — |
| Reactant | HCID 19759235 | HCID 19759235 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | HCID 19759462 | HCID 19759462 | 34.7% |
Reaction Steps
To a solution of 1-(4-ethoxycarbonylphenyl)-4-hydroxymethylpyrrole-2-carbonitrile (500 mg) in dichloromethane (5.5 ml) was added trifluoroacetic acid (2.8 ml) and triethylsilane (652 μl) in that order at 5° C. under nitrogen. The mixture was stirred at 5° C. for one and half hours and at ambient temperature for one hour and then poured into a mixture of diethyl ether and n-hexane (1:1). The mixture was washed with saturated sodium bicarbonate solution and brine, dried, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (elution by ethyl acetate/n-hexane=1/10) to yield 1-(4-ethoxycarbonylphenyl)-4-methylpyrrole-2-carbonitrile (163 mg) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05210092 |
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| Source dataset | uspto-grants-1993_05 |
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| ORD ID | ord-b5009f5feb0f4131a6bdf1132bcb123c |
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| Source note | uspto-grants-1993_05 |
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