HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cerium(III) chloride → HCID 59226486, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cerium(III) chloride | HCID 24636 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | 3-(3-Nitropyridin-4-yl)cyclohex-2-enone | HCID 59226544 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 59226486 | HCID 59226486 | 55.3% |
Reaction Conditions
| Temperature | 0 °C |
|---|
Reaction Steps
To a solution of 3-(3-nitropyridin-4-yl)cyclohex-2-en-1-one (1.9 g, 8.7 mmol) and cerium trichloride (4.2 g, 11 mmol) in EtOH (30 mL) at 0° C., sodium tetrahydroborate (0.43 g, 11 mmol) was slowly added. The reaction mixture was stirred at 0° C. for 2 h, then quenched with water (40 mL). After vacuum filtration, the residue was diluted with EtOAc. The aqueous layer was extracted three times with EtOAc. The combined organic layers were dried, filtered and concentrated under reduced pressure to give a crude product, which was further purified by silica gel column chromatography (eluting with 0-30% MeOH in EtOAc) to give the sub-title compound (1.06 g, 55%). LCMS calc. for C11H13NO3 (M+H)+: m/z=221.1. Found: 221.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09278950B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-eca8f2868b0140bcb8477c85625c7956 |
| Source note | uspto-grants-2016_03 |