2-(4-(benzyloxy)-3-(methoxymethoxy)phenyl)-3,7-bis(methoxymethoxy)-4H-chromen-4-one → 2-(4-hydroxy-3-(methoxymethoxy)phenyl)-3,7-bis(methoxymethoxy)-4H-chromen-4-one

HRID 1879558Notes

Reaction equation

HRID 1879558 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]3[C:22]([C:23](=[O:29])[C:24]=2[O:25][CH2:26][O:27][CH3:28])=[CH:21][CH:20]=[C:19]([O:30][CH2:31][O:32][CH3:33])[CH:18]=3)=[CH:11][C:10]=1[O:34][CH2:35][O:36][CH3:37])C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]3[C:22]([C:23](=[O:29])[C:24]=2[O:25][CH2:26][O:27][CH3:28])=[CH:21][CH:20]=[C:19]([O:30][CH2:31][O:32][CH3:33])[CH:18]=3)=[CH:11][C:10]=1[O:34][CH2:35][O:36][CH3:37]

Participants

4

Reactant 1

HCID 669339302-(4-(benzyloxy)-3-(methoxymethoxy)phenyl)-3,7-bis(methoxymethoxy)-4H-chromen-4-one

Product 1

HCID 669340932-(4-hydroxy-3-(methoxymethoxy)phenyl)-3,7-bis(methoxymethoxy)-4H-chromen-4-oneYield 99.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 2-(4-(benzyloxy)-3-(methoxymethoxy)phenyl)-3,7-bis(methoxymethoxy)-4H-chromen-4-one (55 mg, 0.108 mmol) in 10 mL MeOH was added Palladium on activated carbon (20 mg). The mixture was stirred at rt under H2 atmosphere for 2 h. Solid was filtered off and the filtrate was concentrated to afford 2-(4-hydroxy-3-(methoxymethoxy)phenyl)-3,7-bis(methoxymethoxy)-4H-chromen-4-one as a yellow solid (45 mg, 99%). This material was used directly for the next reaction without purification. MS (ESI) m/z 419 (M+H+).

Workup

  1. filtrationSolid was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-11c2c8d2a8cd46c5b67221b238713980
Source dataset
uspto-grants-2012_11
Patent number
US08318132B2

Reaction notes

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