Methyl 2-(3-ethoxycarbonyl-2-oxo-propylsulfanyl)-benzoate → Methyl 3-ethoxycarbonylmethyl-benzo[b]thiophene-7-carboxylate

HRID 221931노트

반응식

HRID 221931 반응식
[CH2:1]([O:3][C:4]([CH2:6][C:7](=O)[CH2:8][S:9][C:10]1[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13])=[O:5])[CH3:2]>O>[CH2:1]([O:3][C:4]([CH2:6][C:7]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[C:10]=2[S:9][CH:8]=1)=[O:5])[CH3:2]

참가 물질

3

반응물 1

HCID 21761900Methyl 2-(3-ethoxycarbonyl-2-oxo-propylsulfanyl)-benzoate

생성물 1

HCID 59488809Methyl 3-ethoxycarbonylmethyl-benzo[b]thiophene-7-carboxylate수율 37%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Under a nitrogen stream, to methyl 2-(3-ethoxycarbonyl-2-oxo-propylsulfanyl)-benzoate (8.02 g, 27.1 mmol) was added polyphosphoric acid (25 g) at room temperature, and the resultant solution was stirred for 1 hour at 80° C. Under ice-cooling, to the solution was added water, and the resultant mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate and dried over anhydrous magnesium sulfate. Solvent was then removed by distillation under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:3)), to thereby obtain the titled compound (2.77 g, 37%).

후처리

  1. temperatureUnder ice-cooling, to the solution
  2. extractionthe resultant mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customSolvent was then removed by distillation under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:3))

출처 및 근거

ORD 기록
ord-39636c6dcbc641b99fe8561ab5d59484
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207134B2

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