HuagongsheHuagongshe Chemistry Print Report · For research reference only
Piperidine → 4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]1-oxo-2-propenyl]-2H-1-benzopyran-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | 3-Chloro-4-(trifluoromethoxy)benzaldehyde | HCID 2778891 | — |
| Reactant | 3-Acetyl-4-hydroxy-2H-chromen-2-one | HCID 54677403 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Product | 4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]1-oxo-2-propenyl]-2H-1-benzopyran-2-one | HCID 76211114 | 36.2% |
Reaction Steps
A mixture of 2.25 g of 3-acetyl-4-hydroxy-2H-1-benzopyran-2-one, 2.25 g of 3-chloro-4-(trifluoromethoxy)benzaldehyde, 20 ml of chloroform and 0.7 ml of piperidine was heated under refluxing for 2 hours and 30 minutes. After cooled to room temperature, the reaction mixture was concentrated under reduced pressure, and the residue was subjected to column chromatography. Resulting crystals were washed with 40 ml of t-butyl methyl ether to obtain 1.49 g of 4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-2H-1-benzopyran-2-one [Compound No. (1c-6)] was obtained as a yellow crystal.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08524729B2 |
| Source dataset | uspto-grants-2013_09 |
| ORD ID | ord-f556d4fe01f1480cb1a856a18b6c926a |
| Source note | uspto-grants-2013_09 |