LY88074 Trimethyl ether → 2-(4-Methoxyphenyl)-3-(4-Hydroxybenzoyl)-6-Methoxybenzo[b]thiophene

HRID 234790

Reaktionsgleichung

Reaktionsgleichung von HRID 234790
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=3)=[O:12])=[C:9]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[S:8][C:7]=2[CH:29]=1.C(S)C.[Na]>CN(C=O)C.O.CCOC(C)=O.Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=3)=[O:12])=[C:9]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[S:8][C:7]=2[CH:29]=1

Komponenten

7

Edukt 2

HCID 9953060LY88074 Trimethyl etherHCID 45051917HCID 45051917, Verbindung

Produkt 1

HCID 98651972-(4-Methoxyphenyl)-3-(4-Hydroxybenzoyl)-6-Methoxybenzo[b]thiophene

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of 0.4 g (1 mmol) of [6-Methoxy-2-(4-methoxyphenyl)benzo[b]thien-3-yl][4-methoxyphenyl]methanone in 2 mL of DMF was added to a solution of 3 mL of 0.5M sodium ethanethiol in DMF. The reaction mixture was heated to 80° C. for 4 hours. The reaction mixture was allowed to cool and diluted with 10 mL of water and 10 mL of EtOAc and neutralized with 1N HCl. The reaction mixture was extracted three times with 30 mL portions of EtOAc. The combined organic extracts were washed four times with 20 mL portions of brine and dried with MgSO4 and evaporated to dryness. The crude product was chromatographed on silica eluting with 30% EtOAc in hexane, and evaporated to dryness. This yielded 0.31 g of the title compound as a yellow solid.

Aufarbeitung

  1. temperatureto cool
  2. extractionThe reaction mixture was extracted three times with 30 mL portions of EtOAc
  3. washThe combined organic extracts were washed four times with 20 mL portions of brine
  4. dry with materialdried with MgSO4
  5. customevaporated to dryness
  6. customThe crude product was chromatographed on silica eluting with 30% EtOAc in hexane
  7. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-7df6a894b87446858f7b70e9573da166
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05596106

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