Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sulfuric acid magnesium salt (1:1) | HCID 24083 | — |
| Reactant | Diisobutylaluminumhydride | HCID 21225700 | — |
| Reactant | HCID 66924741 | HCID 66924741 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 66924956 | HCID 66924956 | 88.1% |
Reaction Steps
A solution (30 mL) of ethyl 5-(pyridin-2-yl)-1H-pyrrole-3-carboxylate (1.62 g) in tetrahydrofuran was cooled to −50° C., and a 1.5 mol/L solution (15 mL) of diisobutylaluminum hydride in toluene was added dropwise by small portions. The mixture was further stirred at 0° C. for 1 hr, water (3 mL) was added to the reaction mixture and the mixture was stirred at room temperature for 1 hr. Celite and anhydrous magnesium sulfate were added and the mixture was further stirred for 15 min and filtrated. The obtained filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=1:1→1:3) to give the title compound as colorless crystals (yield 1.15 g, 88%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08048909B2 |
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| Source dataset | uspto-grants-2011_11 |
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| ORD ID | ord-484845b328664b5482792a58528b1fd8 |
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| Source note | uspto-grants-2011_11 |
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