Ethyl 2-(4-(benzyloxy)-2-methoxybenzylidene)-3-oxobutanoate → Ethyl 2-(4-hydroxy-2-methoxybenzyl)-3-oxobutanoate

HRID 2387850Notes

Reaction equation

HRID 2387850 reaction equation
C([O:8][C:9]1[CH:24]=[CH:23][C:12]([CH:13]=[C:14]([C:20](=[O:22])[CH3:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:11]([O:25][CH3:26])[CH:10]=1)C1C=CC=CC=1>CCOC(C)=O.[Pd]>[OH:8][C:9]1[CH:24]=[CH:23][C:12]([CH2:13][CH:14]([C:20](=[O:22])[CH3:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:11]([O:25][CH3:26])[CH:10]=1

Participants

4

Reactant 1

HCID 68413560Ethyl 2-(4-(benzyloxy)-2-methoxybenzylidene)-3-oxobutanoate

Product 1

HCID 68415133Ethyl 2-(4-hydroxy-2-methoxybenzyl)-3-oxobutanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the product from step (i) (40 g) and 5% Pd—C (3 g) in EtOAc were hydrogenated at 3 Bar for 48 h. The mixture was filtered through celite and evaporated under reduced pressure. The residue was purified by column chromatography eluting with 30% EtOAc/iso-hexane to afford the subtitle compound, 23.35 g.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customevaporated under reduced pressure
  3. customThe residue was purified by column chromatography
  4. washeluting with 30% EtOAc/iso-hexane

Sources & evidence

ORD record
ord-bff39c72e56e4434a022a207766a267a
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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