Tert-Butyl nitrite → Ethyl 5-phenylthiophene-3-carboxylate

HRID 1914535ノート

反応式

HRID 1914535 の反応式
C(ON=O)(C)(C)C.[CH2:8]([O:10][C:11]([C:13]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[S:15][C:14]=1[NH2:24])=[O:12])[CH3:9]>[Cu](Cl)Cl>[CH2:8]([O:10][C:11]([C:13]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[S:15][C:14]=1[NH2:24])=[O:12])[CH3:9].[CH2:8]([O:10][C:11]([C:13]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[S:15][CH:14]=1)=[O:12])[CH3:9]

参加物

5

反応物 2

HCID 10906Tert-Butyl nitriteHCID 638860ethyl 2-amino-5-phenylthiophene-3-carboxylate

生成物 2

HCID 638860ethyl 2-amino-5-phenylthiophene-3-carboxylateHCID 58110324Ethyl 5-phenylthiophene-3-carboxylate収率 212.1%

試薬・触媒・溶媒 1

HCID 24014Cupric Chloride触媒

実験手順

2-Amino-5-phenyl thiophene-3-carboxylic ethyl ester was prepared according to the method described by Hwang et al., 2001. t-Butylnitrite (1.6 mL, 13.3 mmol) and anhydrous copper (II) chloride (25 mmol) were dissolved in IMS (100 mL). To this was added 2-amino-5-phenyl-thiophene-3-carboxylic acid ethyl ester (6.9 mmol) in one portion and the reaction was stirred for 1 hour. The reaction was quenched with saturated aqueous ammonium chloride (2 mL) and the solvent evaporated. The resulting slurry was partitioned between DCM and water. The organic solution was separated and dried over magnesium sulfate, filtered and the solvent evaporated to give the title compound as a brown oil (1.7 g, 98%). 1H NMR (400 MHz, CHCl3-d): δ 8.0 (s, 1H), 7.75 (s, 1H), 7.65 (d, 2H), 7.4 (t, 2H), 7.3 (m, 1H), 4.35 (q, 2H), 1.4 (t, 3H).

後処理

  1. customThe reaction was quenched with saturated aqueous ammonium chloride (2 mL)
  2. customthe solvent evaporated
  3. customThe resulting slurry was partitioned between DCM and water
  4. customThe organic solution was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent evaporated

出典と根拠

ORDレコード
ord-882db65f180944a48287ea46d7b1f656
出典データセット
uspto-grants-2013_12
特許番号
US08614209B2

反応ノート

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