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

HRID 446811Notes

Reaction equation

HRID 446811 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH2:19][O:18][C:17](=[O:20])[C:16]=2[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH2:19][O:18][C:17](=[O:20])[C:16]=2[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 670755844-(4-(benzyloxy)phenyl)-3-(4-methoxyphenyl)furan-2(5H)-one

Product 1

HCID 116948254-(4-hydroxyphenyl)-3-(4-methoxyphenyl)furan-2(5H)-oneYield 81%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a 0° C. solution of 4-(4-(benzyloxy)phenyl)-3-(4-methoxyphenyl)furan-2(5H)-one (1.5 g, 0.004 mol) in MeOH (50 mL) was added Pd(OH)2 (150 mg, 1.068 mol) under an inert atmosphere. The reaction mixture was then stirred under a hydrogen atmosphere for 2 h at RT, filtered through a pad of Celite® and the filtrate was concentrated in vacuo to afford 4-(4-hydroxyphenyl)-3-(4-methoxyphenyl)furan-2(5H)-one (900 mg, 81%) as a solid.

Workup

  1. filtrationfiltered through a pad of Celite®
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2a42a10185754612be6e39f3270f289c
Source dataset
uspto-grants-2013_07
Patent number
US08481534B2

Reaction notes

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