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

HRID 1516587Notes

Reaction equation

HRID 1516587 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)=[C:7](OC)[C:6]=1[O:34][CH3:35])[CH3:2].[C:37](OCC)(=[O:39])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:34][CH2:35][O:39][CH3:37])[CH3:2]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 685077024-[4-(2-Benzyloxyphenyl)-3-cyanopyrrole-1-yl]-2-methoxy-methoxy-benzoic acid ethyl ester

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-[4-(2-benzyloxyphenyl)-3-cyanopyrrole-1-yl]-2-methoxy-methoxy-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-5ad66f57b43b458b9d8ecc01a3c47880
Source dataset
uspto-grants-2012_07
Patent number
US08227500B2

Reaction notes

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