Hydrochloric Acid → Ethyl benzo[b]thiophene-5-carboxylate

HRID 250243Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 250243
Cl.[S:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:5]=2[CH:4]=[CH:3]1.[CH2:14](O)[CH3:15]>>[CH2:14]([O:12][C:11]([C:9]1[CH:8]=[CH:7][C:6]2[S:2][CH:3]=[CH:4][C:5]=2[CH:10]=1)=[O:13])[CH3:15]

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 27954441-Benzothiophene-5-carboxylic acid

Produkt 1

HCID 14792358Ethyl benzo[b]thiophene-5-carboxylateAusbeute 89 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A saturated solution of HCl in ethanol (15 mL) is added to benzothiophene-5-carboxylic acid (1 g, 5.44 mmol) and the reaction mixture is stirred at 80° C. overnight. The solvent is removed under reduced pressure and diethyl ether and saturated sodium bicarbonate are added to the residue. The layers are separated. The organic layer is washed with saturated sodium bicarbonate and water, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to yield the title compound (1.0 g, 89%) as a pale brown oil. 1H NMR (CDCl3): δ 8.54 (s, 1H), 8.01 (d, 1H, J=8.1 Hz), 7.92 (d, 1H, J=8.1 Hz), 7.51 (d, 1H, J=5.4 Hz), 7.42 (d, 1H, J=5.4 Hz), 4.42 (c, 2H, J=6.8 Hz), 1.43 (t, 3H, J=6.8 Hz).

Aufarbeitung

  1. customThe solvent is removed under reduced pressure and diethyl ether and saturated sodium bicarbonate
  2. additionare added to the residue
  3. customThe layers are separated
  4. washThe organic layer is washed with saturated sodium bicarbonate and water
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a58832ce62644a6bbb2b60a0d4f2fd8f
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863302B2

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