Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium bis(2-methoxyethoxy)aluminiumhydride | HCID 21584525 | — |
| Reactant | HCID 58452414 | HCID 58452414 | — |
| Solvent | MeOH tetrahydrofuran | HCID 21899815 | — |
| Product | HCID 58452777 | HCID 58452777 | 74% |
Reaction Steps
Water (3 mL) and Oxone(R) (853 mg) were sequentially added to a solution of 3-chloro-6-{(E)-2-cyclopentyl-1-[4-(methylsulfanyl)phenyl]ethenyl}pyridin-2(1H)-one obtained in Example 1-1 (160 mg) in THF-methanol (1:1, 6 mL), and the mixture was stirred at room temperature for one hour. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:hexane=10:0→9:1). The resulting crude product was recrystallized from a chloroform:ethyl acetate:hexane (1:1:1, 6 mL) solution to give the title compound as a colorless powder (130 mg, 74%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08822503B2 |
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| Source dataset | uspto-grants-2014_09 |
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| ORD ID | ord-a556f9cc74d7401ab77f91387e02e919 |
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| Source note | uspto-grants-2014_09 |
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