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

HRID 1617198Notes

Reaction equation

HRID 1617198 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-690eaefada934d159f36b4f1461442e1
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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