Acetic Acid → methyl 4H-thieno(3,2-b)pyrrole-2-carboxylate

HRID 1442540ノート

反応式

HRID 1442540 の反応式
CN(C)/[CH:3]=[CH:4]/[C:5]1[S:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][C:6]=1[N+:14]([O-])=O.C(O)(=O)C>O1CCCC1.[Pd]>[S:9]1[C:5]2[CH:4]=[CH:3][NH:14][C:6]=2[CH:7]=[C:8]1[C:10]([O:12][CH3:13])=[O:11]

参加物

5

反応物 2

HCID 176Acetic AcidHCID 12110978methyl (E)-5-(2-dimethylaminovinyl)-4-nitrothiophene-2-carboxylate

生成物 1

HCID 12110979methyl 4H-thieno(3,2-b)pyrrole-2-carboxylate収率 87%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of methyl (E)-5-(2-dimethylaminovinyl)-4-nitrothiophene-2-carboxylate (20 g, 78 mmol), 5% palladium/carbon (2 g) and acetic acid (20 ml) in tetrahydrofuran (300 ml) was stirred under hydrogen atmosphere (3.5 atm) at room temperature for 16 hr. The reaction mixture was filtered through celite and concentrated under reduced pressure. Diethyl ether (300 ml) was added to the residue. The mixture was washed successively with 1N hydrochloric acid (100 ml×2), water (100 ml), saturated aqueous sodium hydrogen carbonate solution (100 ml×2) and saturated brine (100 ml), and dried over magnesium sulfate. Filtration and concentration under reduced pressure gave methyl 4H-thieno[3,2-b]pyrrole-2-carboxylate (12 g, yield 87%).

後処理

  1. filtrationThe reaction mixture was filtered through celite and
  2. concentrationconcentrated under reduced pressure
  3. additionDiethyl ether (300 ml) was added to the residue
  4. washThe mixture was washed successively with 1N hydrochloric acid (100 ml×2), water (100 ml), saturated aqueous sodium hydrogen carbonate solution (100 ml×2) and saturated brine (100 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationFiltration and concentration under reduced pressure

出典と根拠

ORDレコード
ord-239187d8baf84a19bab1c1aad3a75b0c
出典データセット
uspto-grants-2010_02
特許番号
US07659263B2

反応ノート

読み込み中…