2-Acetylamino-4,5,6,7-tetrahydrobenzothiophene-3-carboxylic acid ethyl ester → Ethyl 2-(acetylamino)-7-oxo-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate

HRID 1351242

反応式

HRID 1351242 の反応式
[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH2:18][CH2:17][CH2:16][CH2:15][C:8]=2[S:9][C:10]=1[NH:11][C:12](=[O:14])[CH3:13])=[O:5])[CH3:2].S([O-])([O-])(=O)=[O:20].[Ce+4].S([O-])([O-])(=O)=O>C(O)(=O)C.O>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH2:18][CH2:17][CH2:16][C:15](=[O:20])[C:8]=2[S:9][C:10]=1[NH:11][C:12](=[O:14])[CH3:13])=[O:5])[CH3:2]

参加物

5

反応物 2

HCID 986822-Acetylamino-4,5,6,7-tetrahydrobenzothiophene-3-carboxylic acid ethyl esterHCID 159684Ceric sulfate

生成物 1

HCID 2830693Ethyl 2-(acetylamino)-7-oxo-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate収率 29.9%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

To a suspension of 2-Acetylamino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester (140 g) in acetic acid (1.5 L) and water (1.5 L) was added gradually cerium (IV) sulfate 4 hydrate (900 g) with vigorously stirring. After the solution was stirred overnight, the solid was removed by filtration and the filtrate was concentrated. The solution was then neutralized with aqueous ammonia and extracted 3 times with ethyl acetate-tetrahydrofuran (=4:1). The organic layers were combined and evaporated in vacuo. The resulting solid was washed with tetrahydrofuran to provide the title compound (44 g) as a pale yellow solid.

後処理

  1. stirringAfter the solution was stirred overnight
  2. customthe solid was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. extractionextracted 3 times with ethyl acetate-tetrahydrofuran (=4:1)
  5. customevaporated in vacuo
  6. washThe resulting solid was washed with tetrahydrofuran

出典と根拠

ORDレコード
ord-fb6ee0870ef94dcd9f3de61a065dd6d4
出典データセット
uspto-grants-2007_05
特許番号
US07217723B2

関連ノート

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