Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Resorcinol | HCID 5054 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Ethyl 3-(furan-3-yl)-3-oxopropanoate | HCID 336409 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | 4-(3-Furyl)-7-hydroxycoumarin | HCID 15780550 | — |
Reaction Steps
A mixture of ethyl 3-oxo-3-(3-furyl)propionate (Aldrich; 3.17 g) and resorcinol (3.83 g) was treated with polyphosphoric acid (15 g) and heated to 110° C. under nitrogen. After 2 hr., the tarry mixture was cooled, then H2O and THF were added until a solution was obtained. Brine and EtOAc were added, the organic layer was removed and washed twice with brine. Chromatography of the residue, after concentration, using hexane/EtOAc 2:1 followed by swishing the product with ether afforded the title compound as a solid, m.p. 229-232° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05424320 |
|---|
| Source dataset | uspto-grants-1995_06 |
|---|
| ORD ID | ord-65a6166d0e6c4a2595139d8c06654b50 |
|---|
| Source note | uspto-grants-1995_06 |
|---|
