Hydrochloric Acid → HCID 69424568, compound

HRID 350050Notes

Reaction equation

HRID 350050 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][O:7][C:8]1[CH:32]=[CH:31][C:11]([CH2:12][N:13]2[CH:17]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:15]([CH2:24][CH2:25][C:26]([O:28]CC)=[O:27])=[CH:14]2)=[CH:10][CH:9]=1.[OH-].[Na+].O1CCCC1.Cl>C(O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][O:7][C:8]1[CH:32]=[CH:31][C:11]([CH2:12][N:13]2[CH:17]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:15]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:14]2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 69421811HCID 69421811, compound

Product 1

HCID 69424568HCID 69424568, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-[1-[4-(2-furylmethoxy)benzyl]-4-phenyl-3-pyrrolyl]propionate (624 mg), 1N aqueous sodium hydroxide solution (3 ml), tetrahydrofuran (6 ml), and ethanol (6 ml) was stirred at room temperature for 3 hours, and 1N hydrochloric acid (3 ml) was added to the mixture, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), then concentrated. The residue was subjected to silica gel column chromatography, and 3-[1-[4-(2-furylmethoxy)benzyl]-4-phenyl-3-pyrrolyl]propionic acid (386 mg, yield: 66%) was obtained as an oily substance from the fraction eluted with ethyl acetate-hexane (1:1, volume ratio).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-70dfe0c4e52a48f8afed5f001def0524
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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