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

HRID 478036
ノート
印刷プレビュー

反応式

HRID 478036 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

HCID 540490452-Methylsulphonyl-4-phenylbutyric acid ethyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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)

後処理

  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)

出典と根拠

ORDレコード
ord-d0930861d2ba43478dd4e4cb4a4fb6e7
出典データセット
uspto-grants-1989_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04889869

反応ノート

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