Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | HCID 12926196 | HCID 12926196 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 22636246 | HCID 22636246 | 74.4% |
Reaction Steps
To a mixture of LiAlH4 (1.1 g) in THF (15 mL) is added a solution of ethyl 2-(4-fluorophenyl)hydrazinecarboxylate (1.9 g, 9.59 mmol) in THF (10 mL) dropwise under nitrogen in an ice-salt bath. After the addition, the ice bath is removed and the mixture is heated to 60° C. overnight. The reaction is cooled and quenched with water. The precipitate is filtered and washed with EtOAc. The organic phase is separated, dried over Na2SO4, and concentrated. The residue is purified by flash chromatography, eluting with PE:EtOAc (80:1 to 60:1) to afford the title compound (1 g, 74% yield). MS (m/z): 141 (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-def9faf62545479fb67b17bad0331288 |
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| Source note | uspto-grants-2011_10 |
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