Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | HCID 10910588 | HCID 10910588 | — |
| Reactant | HCID 178420632 | HCID 178420632 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 68511971 | HCID 68511971 | 96% |
Reaction Steps
To a solution of 2-methyl-5-phenylthiophene-3-carbaldehyde (1.72 g) synthesized above in tetrahydrofuran (40 mL) was added dropwise 1.0M cyclohexylmagnesium bromide-tetrahydrofuran solution (12.8 mL) at 0° C., and the mixture was stirred for 2 hr. 1.0M Cyclohexylmagnesium bromide-tetrahydrofuran solution (5 mL) was added dropwise again, and the mixture was further stirred at 0° C. for 1 hr. 1N Hydrochloric acid was added to quench the reaction, tetrahydrofuran was evaporated using evaporator, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20% ethyl acetate/hexane) to give the title compound (2.33 g, 96%) as a pale-yellow solid.
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-4307c2b36b4a4dbd999aa6597e351d60 |
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| Source note | uspto-grants-2012_11 |
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