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

HRID 2305841Notes

Reaction equation

HRID 2305841 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-(4methoxy-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 The residue
  4. customobtained
  5. extractionwas extracted with chloroform
  6. washwashed well with water
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated The product
  10. customobtained
  11. customwas purified by silica-gel column chromatography
  12. washby eluting it with 30% ethyl acetate

Sources & evidence

ORD record
ord-9a2aa37ff42a4c8c8bfafd56b2b1da7b
Source dataset
uspto-grants-2002_08
Patent number
US06441023B1

Reaction notes

Loading…