Hydrochloric Acid → 2-(4-Methoxyphenyl)-3-(4-Hydroxybenzoyl)-6-Methoxybenzo[b]thiophene

HRID 354085

Reaktionsgleichung

Reaktionsgleichung von HRID 354085
C(S)C.C([Li])CCC.[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]2[C:18]([C:19]([C:21]3[CH:26]=[CH:25][C:24]([O:27]C)=[CH:23][CH:22]=3)=[O:20])=[C:17]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[S:16][C:15]=2[CH:37]=1.Cl>O1CCCC1.CN(C)C=O>[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]2[C:18]([C:19]([C:21]3[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=3)=[O:20])=[C:17]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[S:16][C:15]=2[CH:37]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 9953060LY88074 Trimethyl etherHCID 178418339Butyllithium

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethanethiol (538 mL, 7.27 mmol) in 1.88 mL of tetrahydrofuran, cooled to −30° C. was added n-butyllithium (2.57 mL, 2.5 M, 6.42 mmol) and the reaction was warmed to room temperature. Dimethylformamide (1 mL) was added then the product from Step 1 (1.73 g, 4.3 mmol) in 2.7 mL of dimethylformamide. The reaction was heated at 58° C. for two hours then at 80° C. for 1 hour. The cooled reaction was poured into 33 mL oh 1N hydrochloric acid and extracted with ethyl acetate. The combined organic layers was washed with brine and dried over anhydrous magnesium sulfate. After filtration, concentration and silica gel column chromatography using 15% ethyl acetate -hexanes as eluant the title compound (1.17 g) was obtained.

Aufarbeitung

  1. temperatureThe reaction was heated at 58° C. for two hours
  2. customThe cooled reaction
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration, concentration and silica gel column chromatography
  7. customwas obtained

Quellen und Nachweise

ORD-Eintrag
ord-833a6e54d2d04733b394359c809d7828
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06756388B1

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