3-(4-(benzyloxy)phenyl)-4-(pyridin-4-yl)furan-2(5H)-one → 3-(4-hydroxyphenyl)-4-(pyridin-4-yl)furan-2(5H)-one

HRID 446795Notes

Reaction equation

HRID 446795 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16](=[O:26])[O:17][CH2:18][C:19]=2[C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>Br.CC(O)=O>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:16](=[O:26])[O:17][CH2:18][C:19]=2[C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)=[CH:13][CH:14]=1

Participants

3

Reactant 1

HCID 670750913-(4-(benzyloxy)phenyl)-4-(pyridin-4-yl)furan-2(5H)-one

Product 1

HCID 1361733353-(4-hydroxyphenyl)-4-(pyridin-4-yl)furan-2(5H)-oneYield 138.2%

Reagents, catalysts & solvents 1

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

A mixture of 3-(4-(benzyloxy)phenyl)-4-(pyridin-4-yl)furan-2(5H)-one (1.0 g, 0.002 mol) in 33% HBr/AcOH (50 mL) was refluxed for 3 h. The reaction mixture was quenched with a saturated NaHCO3 solution and extracted with EtOAc (2×50 mL). The combined organic layers were washed with water, dried over Na2SO4, filtered, and concentrated in vacuo to afford 3-(4-hydroxyphenyl)-4-(pyridin-4-yl)furan-2(5H)-one (0.7 g, 95%).

Workup

  1. temperaturewas refluxed for 3 h
  2. customThe reaction mixture was quenched with a saturated NaHCO3 solution
  3. extractionextracted with EtOAc (2×50 mL)
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3c1251d7b5a64045bd4f21be781b66f1
Source dataset
uspto-grants-2013_07
Patent number
US08481534B2

Reaction notes

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