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

HRID 1914535Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1914535
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]

Komponenten

5

Edukt 2

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

Produkt 2

HCID 638860ethyl 2-amino-5-phenylthiophene-3-carboxylateHCID 58110324Ethyl 5-phenylthiophene-3-carboxylateAusbeute 212,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24014Cupric ChlorideKatalysator

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-882db65f180944a48287ea46d7b1f656
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614209B2

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