Hydrochloric Acid → 4-Methoxy-3-(2-phenylethyl)benzo[b]thiophene

HRID 230884Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 230884
C([C:4]1[S:8][C:7]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH3:14])[C:6]=2[C:5]=1[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(O)=O.Cl>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[CH3:14][O:13][C:12]1[C:6]2[C:5]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:4][S:8][C:7]=2[CH:9]=[CH:10][CH:11]=1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 231035202-Carboxy-4-methoxy-3-(2-phenylethyl)benzo[b]thiophene

Produkt 1

HCID 231035114-Methoxy-3-(2-phenylethyl)benzo[b]thiopheneAusbeute 89,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23978CopperKatalysatorHCID 7047QuinolineLösungsmittel

Versuchsvorschrift

A suspension of 2-carboxy-4-methoxy-3-(2-phenylethyl)benzo[b]thiophene (1 g) and a catalytic amount of copper powder in quinoline (15 mL) was stirred at 200° C. for 2 hours. The reaction mixture was cooled to room temperature and poured into 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with 1 mol/L hydrochloric acid and water, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=5/1) to give the title compound (0.77 g).

Aufarbeitung

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with 1 mol/L hydrochloric acid and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=5/1)

Quellen und Nachweise

ORD-Eintrag
ord-50415b8d3c7d4c0d81ff32d21763ee6f
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566699B2

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