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

HRID 1178616

반응식

HRID 1178616 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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, 1 H), 6.95 (m, 1 H), 7.32 (dd, J=5, 1 Hz, 1H); MS 185.0 (M+H)+

후처리

  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

출처 및 근거

ORD 기록
ord-e7b935dd302b40d2b1111f08492c7f14
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07276519B2

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