Ethanol → Ethyl 3-[1-(3,5-dihydroxybenzyl)-4-phenyl-3-pyrrolyl]propionate

HRID 349902Notes

Reaction equation

HRID 349902 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:31]=[C:32]([O:34]CC2C=CC=CC=2)[CH:33]=1)[CH2:12][N:13]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15](/[CH:24]=[CH:25]/[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:14]1)C1C=CC=CC=1.C(O)C>[C].[Pd].O1CCCC1>[OH:8][C:9]1[CH:10]=[C:11]([CH:31]=[C:32]([OH:34])[CH:33]=1)[CH2:12][N:13]1[CH:17]=[C:16]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:15]([CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:14]1

Participants

5

Reactant 2

HCID 702EthanolHCID 69421654ethyl(E)-3-[1-(3,5-dibenzyloxybenzyl)-4-phenyl-3-pyrrolyl]propenoate

Product 1

HCID 23024867Ethyl 3-[1-(3,5-dihydroxybenzyl)-4-phenyl-3-pyrrolyl]propionateYield 95%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl(E)-3-[1-(3,5-dibenzyloxybenzyl)-4-phenyl-3-pyrrolyl]propenoate (19.0 g), 5% palladium-carbon (40.0 g), ethanol (200 ml), and tetrahydrofuran (200 ml) was stirred for 4 hours at room temperature under a hydrogen atmosphere. After the palladium-carbon was removed by filtration, the filtrate was concentrated. The residue was subjected to silica gel column chromatography, and ethyl 3-[1-(3,5-dihydroxybenzyl)-4-phenyl-3-pyrrolyl]propionate (12.10 g, yield: 95%) was obtained as an oily substance from the fraction eluted with ethyl acetate-hexane (3:2, volume ratio).

Workup

  1. customAfter the palladium-carbon was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7af82cdbbfdc49c2b8c95ebac2cd2a4f
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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