Benzyl Bromide → 2-(4-Methoxy-benzenesulfonyl)-3-phenyl-propionic acid ethyl ester

HRID 991030Notes

Reaction equation

HRID 991030 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)(=[O:8])=[O:7])[CH3:2].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1OCCOCCOCCOCCOCCOC1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:1]([O:3][C:4](=[O:17])[CH:5]([S:6]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)(=[O:7])=[O:8])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:2]

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 14823722-[(4-Methoxyphenyl)sulfonyl]acetic acid ethyl ester

Product 1

HCID 108934292-(4-Methoxy-benzenesulfonyl)-3-phenyl-propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To stirred solution of the (4-methoxy-benzenesulfonyl)-acetic acid ethyl ester (2.5 g, 10 mmol), benzyl bromide ( 1.8 gm,10 mmol) and 18-Crown-6 (500 mg) in acetone (250 ml) was added K2CO3 (10 gms, excess) and the 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, eluting with 30% ethyl acetate: hexane. The product, 2-(4-methoxy-benzenesulfonyl)-3-phenyl-propionic acid ethyl ester was isolated as a low melting solid. Yield: 3.0 gm 86%; Low melting solid; MS: 349 (M+H)+.

Workup

  1. temperaturethe 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. washeluting with 30% ethyl acetate

Sources & evidence

ORD record
ord-6b34b1d6ce794d30b8a7082f25d57574
Source dataset
uspto-grants-2002_10
Patent number
US06462073B2

Reaction notes

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