Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | HCID 86646399 | HCID 86646399 | — |
| Reactant | HCID 178420632 | HCID 178420632 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 68507978 | HCID 68507978 | 52% |
Reaction Steps
To a solution of 4-methyl-1-[3-(trifluoromethyl)phenyl]-1H-pyrrole-3-carbaldehyde (2.3 g) synthesized above in tetrahydrofuran (20 mL) was added dropwise 1M cyclohexylmagnesium bromide-tetrahydrofuran solution (12 mL) at 0° C. After stirring at 0° C. for 1 hr, an aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The extract was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio) to give the title compound (1.8 g, 52%) as a colorless solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08309580B2 |
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| Source dataset | uspto-grants-2012_11 |
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| ORD ID | ord-a7c7ec7564114114a0bae6d01bce5598 |
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| Source note | uspto-grants-2012_11 |
|---|