Methyl iodide → 2-(4-Methoxy-benzenesulfonyl)-2-methyl-3-phenyl-propionic acid ethyl ester

HRID 2270316Notes

Reaction equation

HRID 2270316 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH:5]([S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].CI.[CH2:27]1OCCOCCOCCOCCOCCOC1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:1]([O:3][C:4](=[O:24])[C:5]([S:13]([C:16]1[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=1)(=[O:14])=[O:15])([CH3:27])[CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 108934292-(4-Methoxy-benzenesulfonyl)-3-phenyl-propionic acid ethyl ester

Product 1

HCID 109484392-(4-Methoxy-benzenesulfonyl)-2-methyl-3-phenyl-propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 2-(4-methoxy-benzenesulfonyl)-3-phenyl-propionic acid ethyl ester (1.0 gm, 3mmol) (example 9), methyl iodide (1 ml, excess) and 18-Crown-6 (500 mg) in acetone (250 ml), K2CO3 (10 gm, excess) was added and the reaction mixture was refluxed for 24 hours. At the end, the reaction mixture was filtered and the acetone layer was concentrated. The residue obtained was extracted with chloroform, washed well with water, dried over anhydrous MgSO4, filtered and concentrated. The product obtained was purified by silica-gel column chromatography by eluting it with 30% ethyl acetate:hexanes to afford 2-(4-methoxy-benzenesulfonyl)-2-methyl-3-phenyl-propionic acid ethyl ester as a colorless oil. Yield 1.0 g, 98%; MS: 349 (M+H)+.

Workup

  1. temperaturethe reaction mixture was refluxed for 24 hours
  2. filtrationAt the end, the reaction mixture was filtered
  3. concentrationthe acetone layer was concentrated
  4. customThe residue obtained
  5. extractionwas extracted with chloroform
  6. washwashed well with water
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe product obtained
  11. customwas purified by silica-gel column chromatography
  12. washby eluting it with 30% ethyl acetate

Sources & evidence

ORD record
ord-cf72853bd6e343879bb30e40919c66e6
Source dataset
uspto-grants-2001_12
Patent number
US06331563B1

Reaction notes

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