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

HRID 565283

반응식

HRID 565283 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-6beca1c808a5402799974d9739ed08a9
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06172057B2

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