Water → HCID 21072938, compound

HRID 1373238Notes

Reaction equation

HRID 1373238 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH2:14][CH2:15][CH2:16][C:17]([O:19]CC)=O)=[CH:9][CH:8]=1)=[O:5])[CH3:2].[H-].[Na+].O>O1CCCC1>[CH2:1]([O:3][C:4](=[O:5])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:14][CH2:15][CH2:16][C:17]2=[O:19])=[CH:9][CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 21072939HCID 21072939, compound

Product 1

HCID 21072938HCID 21072938, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture in tetrahydrofuran (50 ml) of ethyl 4-[4-(ethoxycarbonylmethyl)phenyl]aminobutanoate (2.4 g. 8.3 mmols) and sodium hydride (oily) (0.5 g, 12 mmols) was stirred, while heated under reflux, for 18 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The extract was washed with brine, and then dried with anhydrous magnesium sulfate. This was concentrated under reduced pressure, and the residue was purified through silica gel column chromatography to give a solid of ethyl[4-(2-oxopyrrolidin-1-yl)phenyl]acetate (1.2 g, 59%).

Workup

  1. temperaturewhile heated
  2. temperatureunder reflux, for 18 hours
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationThis was concentrated under reduced pressure
  7. customthe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-a159580196d54c969d94fa5cc5aebe6b
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

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