Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | HCID 86611444 | HCID 86611444 | — |
| Reactant | HCID 178418255 | HCID 178418255 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 69020769 | HCID 69020769 | — |
Reaction Steps
Add phenyl magnesium bromide (192 uL, 0.58 mmol) to 4-cyano-5-ethyl-3-(4-formyl-phenyl)-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester [(0.020 g, 0.64 mmol, prepared in example E-152] in THF with stirring at −78° C. After 30 minutes, gradually allow the reaction mixture to warm to ambient temperature. After 2 hours, pour the reaction mixture into water and extract with EtOAc. Combine the organic extracts, wash with water and brine, dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Purify the residue by flash chromatography eluting with ethyl acetate:hexanes to provide the title compound. Mass spectrum (m/e): 406.1 (M+18).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07625932B2 |
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| Source dataset | uspto-grants-2009_12 |
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| ORD ID | ord-d69cb44178f745b3ba36b3d26c090164 |
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| Source note | uspto-grants-2009_12 |
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