Methanol → 4-(2-Thienyl)butanoic acid methyl ester

HRID 1611490

反応式

HRID 1611490 の反応式
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10].S(=O)(=O)(O)O.[CH3:17]O>>[CH3:17][O:10][C:9](=[O:11])[CH2:8][CH2:7][CH2:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 783864-(2-Thienyl)Butyric Acid

生成物 1

HCID 1407664-(2-Thienyl)butanoic acid methyl ester

実験手順

A mixture of 4-(2-thienyl)butyric acid (4.25 g, 25.0 mmol) and 3 mL of concentrated sulfuric acid in 25 mL of methanol is heated at reflux for 2 hours. The reaction mixture is cooled to room temperature and partitioned between ethyl acetate and saturated aqueous sodium carbonate solution. The organic layer is separated and passed through a short pad of silica gel. The filtrate is concentrated and purified by flash column chromatography eluting with 1:5 ethyl acetate:hexane to provide 4.02 g of 4-thiophen-2-yl-butyric acid methyl ester as a yellow oil, 1H NMR (DMSO-d6) δ 1.85 (quintet, J=7 Hz, 2H), 2.35 (t, J=7 Hz, 2H), 2.81 (t, J=7 Hz, 2H), 3.59 (s, 3H), 6.84 (m, 1H), 6.95 (m, 1H), 7.32 (dd, J=5, 1 Hz, 1H); MS 185.0 (M+H)+.

後処理

  1. temperatureis heated
  2. temperatureat reflux for 2 hours
  3. custompartitioned between ethyl acetate and saturated aqueous sodium carbonate solution
  4. customThe organic layer is separated
  5. concentrationThe filtrate is concentrated
  6. custompurified by flash column chromatography
  7. washeluting with 1:5 ethyl acetate

出典と根拠

ORDレコード
ord-faf3e5369ad34fbdb37d50d149f09561
出典データセット
uspto-grants-2006_01
特許番号
US06987116B2

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