HuagongsheHuagongshe Chemistry Print Report · For research reference only
18-Crown-6 → 7-[(4,6-Dimethoxy-pyrimidin-2-yl)oxy]-3-phenoxy-phthalide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 18-Crown-6 | HCID 28557 | — |
| Reactant | 3-Chloro-7-[(4,6-dimethoxy-pyrimidin-2-yl)oxy]-phthalide | HCID 19927406 | — |
| Reactant | Potassium phenoxide | HCID 23670670 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 7-[(4,6-Dimethoxy-pyrimidin-2-yl)oxy]-3-phenoxy-phthalide | HCID 19927487 | — |
Reaction Steps
A mixture of 1.4 g of 3-chloro-7-[(4,6-dimethoxy-pyrimidin-2-yl)oxy]-phthalide (see Example 85) and 0.63 g of potassium phenolate is heated at reflux temperature in the presence of a spatula tip of 18-crown-6 in 15 ml of acetonitrile. After 19 hours, the reaction mixture is filtered through Celite® and concentrated by evaporation, and the crude product is purified by column chromatography (eluant 25% ethyl acetate/n-hexane) to yield 7-[(4,6-dimethoxy-pyrimidin-2-yl)oxy]-3-phenoxy-phthalide in the form of white crystals, m.p. 155°-157° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05428002 |
| Source dataset | uspto-grants-1995_06 |
| ORD ID | ord-85c2ecd43fd34e1c8da55ae9f327b579 |
| Source note | uspto-grants-1995_06 |