Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Methyl 2-methoxyisonicotinate | HCID 14223465 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (2-Methoxypyridin-4-yl)methanol | HCID 14462410 | 94.5% |
Reaction Steps
To a suspension of lithium aluminum hydride (2.92 g) in diethyl ether (200 ml) and THF (50 mL) was added dropwise a solution of methyl 2-methoxyisonicotinate (8.57 g) in diethyl ether (50 mL) at 0° C., and the reaction mixture was stirred at 0° C. for 20 min. Water (3.0 mL), 4N aqueous sodium hydroxide solution (3.0 mL) and water (9.0 mL) were successively added to the reaction mixture at 0° C., and the mixture was stirred at room temperature for 15 min. The resulting white precipitate was filtered off, and the solvent in the filtrate was evaporated under reduced pressure to give a crude product of the title compound (6.74 g) as a pale-yellow oil. This compound was used for the next step without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09181186B2 |
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| Source dataset | uspto-grants-2015_11 |
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| ORD ID | ord-0108bed5ea1344e6a251bc82f242eb61 |
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| Source note | uspto-grants-2015_11 |
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