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Acetic Acid → 2-Methylsulphonyl-4-phenylbutyric acid ethyl ester

HRID 478036
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HRID 478036 반응식
[CH2:1]([O:3][C:4](=[O:10])[CH2:5][S:6]([CH3:9])(=[O:8])=[O:7])[CH3:2].[OH-].[Na+].[C:13]1([CH2:19][CH2:20]Br)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O)(=O)C>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:10])[CH:5]([S:6]([CH3:9])(=[O:8])=[O:7])[CH2:20][CH2:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 7666Phenethyl bromideHCID 14798Sodium HydroxideHCID 78201Ethyl methanesulfonylacetate

생성물 1

HCID 540490452-Methylsulphonyl-4-phenylbutyric acid ethyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

6.648 g of methylsulphonyl-acetic acid ethyl ester are added dropwise at -30°, within 30 minutes, to 1.745 g of sodium hydroxide dispersion (55% in oil) in 40 ml of DMF. The solution is subsequently stirred for 15 minutes, then heated and, within 150 minutes, under reflux, 7.4 g of 2-phenylethyl bromide in 10 ml of DMF are added dropwise thereto. The reaction mixture is then stirred for 20 minutes, acidified with 12 ml of glacial acetic acid and concentrated by evaporation. The residue is taken up in ethyl acetate, washed with water, dried over magnesium sulphate, concentrated by evaporation and purified by flash chromatography on 700 g of silica gel 60 (eluant D). 1H-NMR (DMSO-d6): 1.35 ppm (t, 3H), 2.6-2.9 (m, 2H); 3.75 (dxd, 1H); 4.25 (q, 2H)

후처리

  1. temperatureheated and, within 150 minutes
  2. temperatureunder reflux
  3. stirringThe reaction mixture is then stirred for 20 minutes
  4. concentrationconcentrated by evaporation
  5. washwashed with water
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated by evaporation
  8. custompurified by flash chromatography on 700 g of silica gel 60 (eluant D)

출처 및 근거

ORD 기록
ord-d0930861d2ba43478dd4e4cb4a4fb6e7
출처 데이터셋
uspto-grants-1989_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04889869

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