Iodoethane → HCID 69358200, compound

HRID 852636Notes

Reaction equation

HRID 852636 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:7]=[C:6]([OH:16])[CH:5]=1.C([O-])([O-])=O.[K+].[K+].[CH2:24](I)[CH3:25]>CN(C=O)C.Cl>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:7]=[C:6]([O:16][CH2:24][CH3:25])[CH:5]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 22252977Methyl 3-hydroxy-5-(2-oxopyrrolidin-1-yl)benzoate

Product 1

HCID 69358200HCID 69358200, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To 3-hydroxy-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (D37) (0.80 g, 3.4 mmol, 1 equiv) dissolved in DMF (10 ml) was added K2CO3 (0.94 g, 6.8 mmol, 2 equiv) and ethyl iodide (1.1 g, 6.8 mmol, 2 equiv). The resulting mixture was heated at 50° C. for 4 h, cooled to room temperature, diluted with 2N aqueous HCl solution (50 ml) and extracted with Et2O (50 ml). The organic phase was then washed with water (50 ml), dried over MgSO4 and concentrated in vacuo to give of 3-ethoxy-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (B11) (0.85 g, 95%) as a brown oil which slowly solidified to a tan solid.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with Et2O (50 ml)
  3. washThe organic phase was then washed with water (50 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-93dc4936bfc2454481df94cb20dbf2db
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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