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

HRID 1914589ノート

反応式

HRID 1914589 の反応式
N(OC(C)(C)C)=O.[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]=1N)=[O:12])[CH3:9]>[Cu](Cl)Cl.[Cl-].[NH4+]>[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 1

HCID 58110324Ethyl 5-phenylthiophene-3-carboxylate収率 73.4%

試薬・触媒・溶媒 2

HCID 24014Cupric Chloride触媒HCID 25517Ammonium Chloride溶媒

実験手順

Anhydrous copper (II) chloride (4 g, 0.03 mol) and tert-butyl nitrite (1.9 mL, 0.019 mol) were dissolved in IMS (100 mL) then treated with 2-amino-5-phenyl-thiophene-3-carboxylic acid ethyl ester (2 g, 8.097 mmol). After 30 minutes saturated aqueous ammonium chloride (20 mL) was added and the mixture left for a further 30 minutes. The resultant precipitate was filtered off and the filtrate was concentrated, washed with DCM, dried and concentrated to give a dark oil which was purified by column chromatography, eluting with 0-35% tert-butyl methyl ether in cyclohexane to afford 5-phenyl-thiophene-3-carboxylic acid ethyl ester as a yellow oil (1.38 g).

後処理

  1. filtrationThe resultant precipitate was filtered off
  2. concentrationthe filtrate was concentrated
  3. washwashed with DCM
  4. customdried
  5. concentrationconcentrated
  6. customto give a dark oil which
  7. customwas purified by column chromatography
  8. washeluting with 0-35% tert-butyl methyl ether in cyclohexane

出典と根拠

ORDレコード
ord-45f921380f6f41569b9950dd09a98e32
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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