HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Anhydride → HCID 178423899, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Anhydride | HCID 7918 | — |
| Reactant | Squaric acid | HCID 17913 | — |
| Reactant | 1-(3,5-dinitrobenzyl)-2,3,3-trimethyl-3H-indolium iodide | HCID 17902140 | — |
| Reactant | 1-(5-Carboxypentyl)-2,3,3-trimethyl-3H-indol-1-ium iodide | HCID 68533817 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Product | HCID 178423899 | HCID 178423899 | — |
Reaction Steps
To 1-(3,5-dinitrobenzyl)-2,3,3-trimethyl-3H-indolium iodide (467 mg) was added 3,4-dihydroxy-3-cyclobuten-1,2-dione (110 mg), 1-(5-carboxypentyl)-2,3,3-trimethyl-3H-indolium iodide (354 mg), pyridine (4.5 ml), acetic acid (4.5 ml) and acetic anhydride (1 ml). The mixture was heated to reflux for 3 hours and the solvent then stripped using rotary evaporation. This crude material was subjected to silica flash column chromatography (eluted with MeOH/DCM). Fractions containing product were combined and stripped of solvent. The resulting material was further purified by reverse phase HPLC (CH3CN/H2O/TFA).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07579140B2 |
| Source dataset | uspto-grants-2009_08 |
| ORD ID | ord-fb931656e7474c99a00cb47b820d5fb4 |
| Source note | uspto-grants-2009_08 |