HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl orthoformate → 6H-Indeno[5,4-d]oxazol-8(7H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl orthoformate | HCID 31214 | — |
| Reactant | 6-Amino-7-hydroxy-2,3-dihydro-1H-inden-1-one hydrobromide | HCID 67353461 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 6H-Indeno[5,4-d]oxazol-8(7H)-one | HCID 57781265 | 362% |
Reaction Steps
6-Amino-7-hydroxyindan-1-one hydrobromide (50 mg, 0.205 mmol) and triethyl orthoformate (128 μL, 0.769 mmol) were heated under reflux in tetrahydrofuran (2.5 mL) for 0.5 hr. The mixture was diluted with ethyl acetate, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→80/20) to give the title compound (21.9 mg, yield from Reference Example 362%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08895591B2 |
| Source dataset | uspto-grants-2014_11 |
| ORD ID | ord-40f48dd0016442b7855ea81bbdc353f3 |
| Source note | uspto-grants-2014_11 |