Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | HCID 59557014 | HCID 59557014 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | HCID 59556976 | HCID 59556976 | 72% |
Reaction Steps
To a mixture of 2-chloro-4-(3-hydroxy-5-oxo-2-propyl-2,5-dihydro-1H-pyrrol-1-yl)benzonitrile (800 mg) and acetic acid (1.82 mL) in acetonitrile (25 mL) was added sodium borohydride (273 mg) at 0° C. in small portions. The mixture was warmed to room temperature and stirred for 1 hr. Water and saturated brine were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (eluent: hexane:ethyl acetate=4:1-Methyl acetate), and recrystallized from tetrahydrofuran-hexane to give the title compound as colorless crystals (yield: 578 mg, 72%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08420694B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-d0a5ca265ddf4627a3109a1067a2a402 |
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| Source note | uspto-grants-2013_04 |
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