Ethyl Acetate → 4-[3-Cyano-4-(2-hydroxyphenyl)pyrrole-1-yl]-2-methoxymethoxy benzoic acid ethyl ester

HRID 570840Notes

Reaction equation

HRID 570840 reaction equation
[CH2:1]([O:3][C:4](=[O:36])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22]CC3C=CC=CC=3)[C:13]([C:30]#[N:31])=[CH:12]2)=[CH:7][C:6]=1[O:32][CH2:33][O:34][CH3:35])[CH3:2].C(OCC)(=O)C>[C].[Pd].CO>[CH2:1]([O:3][C:4](=[O:36])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[OH:22])[C:13]([C:30]#[N:31])=[CH:12]2)=[CH:7][C:6]=1[O:32][CH2:33][O:34][CH3:35])[CH3:2]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 59477635HCID 59477635, compound

Product 1

HCID 594776664-[3-Cyano-4-(2-hydroxyphenyl)pyrrole-1-yl]-2-methoxymethoxy benzoic acid ethyl esterYield 74.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-[4-(2-benzyloxyphenyl)-3-cyanopyrrole-1-yl]-2-methoxymethoxy-benzoic acid ethyl ester (2.3 g) in a mixed solvent of ethyl acetate (20 mL) and methanol (20 mL) was added palladium-carbon powder under an argon atmosphere, and this mixture was stirred at room temperature under a hydrogen atmosphere for 5 hours. The insoluble material was removed by filtration, and this filtrate was concentrated under reduced pressure to give the title compound (1.4 g)

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthis filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-42224e99ea584fe1a0c662b614ecc550
Source dataset
uspto-grants-2015_05
Patent number
US09023882B2

Reaction notes

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