HuagongsheHuagongshe Chemistry Print Report · For research reference only
p-Toluenesulfonic acid → HCID 22801853, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | p-Toluenesulfonic acid | HCID 6101 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | (3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate | HCID 11000244 | — |
| Reactant | Ethylorthoformate | HCID 53630039 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 22801853 | HCID 22801853 | — |
Reaction Steps
7.7 g. of (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3,3,0]octan-3-one was dissolved in 80 ml. of absolute dimethoxyethane, combined with 13.29 g. of ethyl orthoformate in 30 ml. of absolute ethanol and 120 mg. of p-toluenesulfonic acid and stirred overnight at room temperature under argon. Thereafter, the reaction mixture was diluted with ether and shaken in succession three times with 100 ml. of sodium bicarbonate solution as well as 100 ml. of water. The organic phase was dried over sodium sulfate and concentrated to dryness, thus obtaining 8.55 g. of the desired compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04359467 |
| Source dataset | uspto-grants-1982_11 |
| ORD ID | ord-098cb59b90d040bebd97c3f4ef671aa3 |
| Source note | uspto-grants-1982_11 |