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

HRID 221931ノート

反応式

HRID 221931 の反応式
[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]

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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%).

後処理

  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))

出典と根拠

ORDレコード
ord-39636c6dcbc641b99fe8561ab5d59484
出典データセット
uspto-grants-2012_06
特許番号
US08207134B2

反応ノート

読み込み中…