HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → Methyl 2-acetyl-5-oxocyclopentane-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Dimethyl Sulfoxide | HCID 679 | — |
| Reactant | Potassium Acetate | HCID 517044 | — |
| Reactant | Methyl 2-oxobicyclo[3.1.0]hexane-1-carboxylate | HCID 12881134 | — |
| Product | Methyl 2-acetyl-5-oxocyclopentane-1-carboxylate | HCID 13213561 | — |
Reaction Steps
Tanomori et al., Biosci. Biotech. Biochem. 1995, 59: 2091-2093, discloses the reaction of 1-methoxycarbonyl-2-oxo-bicyclo[3.1.0]hexane with potassium acetate and acetic acid in dimethylsulfoxide at 90° C. (4 hours) to obtain 2-methoxycarbonyl-3-acetyl-cyclopentanone. The reference further discloses a formal total synthesis of (+)-carbovir by conversion of the cyclopentanone.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06506908B2 |
| Source dataset | uspto-grants-2003_01 |
| ORD ID | ord-cfd2189ba5ef4e889a92c1466419519b |
| Source note | uspto-grants-2003_01 |