Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | 3-Methyl-5-[4-(trifluoromethyl)phenyl]thiophene-2-carbaldehyde | HCID 21986550 | — |
| Reactant | HCID 178420632 | HCID 178420632 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 68511337 | HCID 68511337 | 51% |
Reaction Steps
To a solution of 3-methyl-5-[4-(trifluoromethyl)phenyl]thiophene-2-carbaldehyde (0.8 g) in tetrahydrofuran (20 mL) was added dropwise 1N cyclohexylmagnesium bromide-tetrahydrofuran solution (5 mL) at 0° C. and, after the completion of the dropwise addition, the mixture was stirred at 0° C. for 30 min. The reaction mixture was treated with 1N hydrochloric acid and poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (0% ethyl acetate/hexane to 20% ethyl acetate/hexane) to give the title compound (0.5 g, 51%) as a yellow crystal.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08309580B2 |
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| Source dataset | uspto-grants-2012_11 |
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| ORD ID | ord-602b33d0ba6e4b368785d80cb4c8c254 |
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| Source note | uspto-grants-2012_11 |
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