Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 1-Fluoro-2-nitrobenzene | HCID 73895 | — |
| Reactant | 1-(1,1-Dimethylethyl) 6-methyl 3-oxohexanedioate | HCID 10911363 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 42643740 | HCID 42643740 | 59.5% |
Reaction Steps
To the suspension of NaH (2.3 g, 57.5 mmol) in DMF (50 mL) was added 2-fluoro-1-nitrobenzene (4.04 g, 28.7 mmol) and 1-(1,1-dimethylethyl) 6-methyl 3-oxohexanedioate (6.6 g, 28.7 mmol). The mixture was heated at 60° C. for 12 h. After cooling to room temperature, the mixture was quenched with NH4Cl aqueous solution, and extracted with ethyl acetate. The combined organic phase was dried over sodium sulfate, filtered, and concentrated. Purification via flash chromatography then afforded the title compound (6.0 g, 45.3% yield). LCMS: rt=4.15 min, [M+H+]=350
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09174968B2 |
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| Source dataset | uspto-grants-2015_11 |
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| ORD ID | ord-af509d7ade4e41dcb6d71254645c05a1 |
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| Source note | uspto-grants-2015_11 |
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