Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Methanol | HCID 887 | — |
| Reactant | 1,3-Diethyl 2-acetylpropanedioate | HCID 136365 | — |
| Reactant | HCID 22636246 | HCID 22636246 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 66767158 | HCID 66767158 | 49.5% |
Reaction Steps
A mixture of 1-(4-fluorophenyl)-2-methylhydrazine (0.6 g, 4.28 mmol), diethyl 2-acetylmalonate (0.96 g, 4.75 mmol), and acetic acid (0.51 g, 8.49 mmol) in water (15 mL) is heated at 115° C. for 3 hours. The reaction is cooled and extracted with EtOAc twice. The organic phase is washed with saturated aqueous sodium chloride, dried over Na2SO4 and concentrated. The residue is purified by column chromatography on silica gel, eluting with DCM:MeOH (from 150:1 to 60:1) to afford the title compound (0.59 g, 49.5% yield). MS (m/z): 279 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08030302B2 |
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| Source dataset | uspto-grants-2011_10 |
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| ORD ID | ord-c85d00b754bb40f3b921767c95e61478 |
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| Source note | uspto-grants-2011_10 |
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