HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → 8-(Benzyloxy)-5-[(2S)oxiranylmethoxy]-3,4-dihydro-2(1H)-quinolinone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester | HCID 146490 | — |
| Reactant | 8-(Benzyloxy)-5-hydroxy-3,4-dihydroquinolin-2(1H)-one | HCID 12751737 | — |
| Solvent | Methyl Ethyl Ketone | HCID 6569 | — |
| Product | 8-(Benzyloxy)-5-[(2S)oxiranylmethoxy]-3,4-dihydro-2(1H)-quinolinone | HCID 23381344 | 82.1% |
Reaction Steps
A mixture of 8-(benzyloxy)-5-hydroxy-3,4-dihydro-2(1H)-quinolinone (0.20 g, 0.743 mmol), (S)-(+)-glycidyl 3-nitrobenzenesulfonate (0.193 g, 0.743 mmol) and potassium carbonate (0.113 g, 0.817 mmol) in 2-butanone (10 mL) was heated at reflux for 16 hours. The solvent was removed in vacuo and the residue purified by flash chromatography (chloroform-methanol, 50:1) to yield the title compound (0.210 g, 0.61 mmol).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06506901B2 |
| Source dataset | uspto-grants-2003_01 |
| ORD ID | ord-60d95559de3842d6aeac341fa2e20646 |
| Source note | uspto-grants-2003_01 |