Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Diisobutylaluminumhydride | HCID 21225700 | — |
| Reactant | HCID 67395699 | HCID 67395699 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67396611 | HCID 67396611 | 41.3% |
Reaction Steps
A solution of ethyl 5-(2-fluoropyridin-3-yl)-4-methyl-1H-pyrrole-3-carboxylate (5.01 g) in tetrahydrofuran (50 mL) was cooled to −78° C., a 1.5 mol/L toluene solution (45 mL) of diisobutylaluminum hydride was added dropwise, and the mixture was stirred at 0° C. for 1 hr. Water was added to the reaction mixture, insoluble materials were filtered off, and the filtrate was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was washed with diisopropyl ether to give the title compound as colorless crystals (yield 1.72 g, 41%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08933105B2 |
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| Source dataset | uspto-grants-2015_01 |
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| ORD ID | ord-a79b489b544741278e195cc588148819 |
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| Source note | uspto-grants-2015_01 |
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