HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hexane → 5-Methyl-1-phenylpyrazole-3-carbaldehyde
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hexane | HCID 8058 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Diisobutylaluminum hydride | HCID 14487 | — |
| Reactant | Ethyl 5-methyl-1-phenyl-1H-pyrazole-3-carboxylate | HCID 10900438 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 5-Methyl-1-phenylpyrazole-3-carbaldehyde | HCID 14135236 | 81.7% |
Reaction Steps
3-Ethoxycarbonyl-1-phenyl-5-methylpyrazole (3.482 g, 15.12 mmol) was dissolved in 20 mL of purified methylene chloride, and then dropwisely added with DIBAL (45.36 mL, 45.36 mmol) at −78° C. and stirred. Termination of the reaction was confirmed by TLC (hexane:ethyl acetate=5:1). Upon completion of reaction, the reaction mixture was dropwisely added with methanol and water, and then extracted with methylene chloride. The resulting organic layer was dried with anhydrous magnesium sulfate and filtered, and the filtrate was concentrated and dried in vacuo to obtain the target compound, 3-formyl-5-methyl-1-phenylpyrazole.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08299072B2 |
| Source dataset | uspto-grants-2012_10 |
| ORD ID | ord-9d59da27d5a34a238938585f29a33a4e |
| Source note | uspto-grants-2012_10 |