Réaction #49847

Équation de réaction

H2O

THF

ethyl 3-oxo-3-(3-furyl)propionate

resorcinol

→

title compound

4-(3-Furyl)-7-hydroxycoumarin

Solvants

Brine

EtOAc

Conditions de réaction

Traitement

1. 1
   Température, the tarry mixture was cooled
2. 2
   Autrewas obtained
3. 3
   Autrethe organic layer was removed
4. 4
   Lavagewashed twice with brine
5. 5
   ConcentrationChromatography of the residue, after concentration

Mode opératoire

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.

Source