Water → 4-(3-Furyl)-7-hydroxycoumarin

HRID 21569Notes

Reaction equation

HRID 21569 reaction equation
O=[C:2]([C:9]1[CH:13]=[CH:12][O:11][CH:10]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:14]1(C=C[CH:19]=[C:17](O)[CH:16]=1)[OH:15].O.C1COCC1>[Cl-].[Na+].O.CCOC(C)=O>[O:11]1[CH:12]=[CH:13][C:9]([C:2]2[C:19]3[C:7](=[CH:8][C:14]([OH:15])=[CH:16][CH:17]=3)[O:6][C:4](=[O:5])[CH:3]=2)=[CH:10]1

Participants

7

Reactant 4

HCID 962WaterHCID 5054ResorcinolHCID 8028TetrahydrofuranHCID 336409Ethyl 3-(furan-3-yl)-3-oxopropanoate

Product 1

HCID 157805504-(3-Furyl)-7-hydroxycoumarin

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
110 °C

Procedure

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.

Workup

  1. temperature, the tarry mixture was cooled
  2. customwas obtained
  3. customthe organic layer was removed
  4. washwashed twice with brine
  5. concentrationChromatography of the residue, after concentration

Sources & evidence

ORD record
ord-65a6166d0e6c4a2595139d8c06654b50
Source dataset
uspto-grants-1995_06
Patent number
US05424320

Reaction notes

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