Methanesulfonic Acid → 4-Methoxy-benzo[b]thiophen-3-yl-acetic acid ethyl ester

HRID 250262ノート

反応式

HRID 250262 の反応式
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][C:6](=O)[CH2:7][S:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)[CH3:2].CS(O)(=O)=O>>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][C:6]1[C:10]2[C:11]([O:15][CH3:16])=[CH:12][CH:13]=[CH:14][C:9]=2[S:8][CH:7]=1)[CH3:2]

参加物

3

反応物 2

HCID 6395Methanesulfonic AcidHCID 21816283Ethyl 4-[(3-methoxyphenyl)sulfanyl]-3-oxobutanoate

生成物 1

HCID 218162724-Methoxy-benzo[b]thiophen-3-yl-acetic acid ethyl ester収率 59%

実験手順

4-(3-methoxy-phenylsulfanyl)-3-oxo-butyric acid ethyl ester (10.9 g, 40.62 mmol) is added to methanesulfonic acid (26.6 mL, 406 mmol). The mixture is stirred at room temperature for 30 minutes. The reaction mixture is poured into ice-water (300 g) and extracted with EtOAc (100 mL×2). The combined organic layers are dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product is purified by flash chromatography eluting with 20% EtOAc/Hexanes. The appropriate fractions are combined and concentrated under reduced pressure to afford the title compound (6.00 g, 59%). ES/MS n/e 251.0 (M+1)

後処理

  1. extractionextracted with EtOAc (100 mL×2)
  2. dry with materialThe combined organic layers are dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product is purified by flash chromatography
  6. washeluting with 20% EtOAc/Hexanes
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-a18fbf41db104f23a8d6e5401c2f5d4d
出典データセット
uspto-grants-2011_01
特許番号
US07863302B2

反応ノート

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