Water → 2'-Methoxy-4'-(thien-2-yl)acetophenone

HRID 1792971

Reaktionsgleichung

Reaktionsgleichung von HRID 1792971
I[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([O:11][CH3:12])[CH:3]=1.[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:12][O:11][C:4]1[CH:3]=[C:2]([C:14]2[S:13][CH:17]=[CH:16][CH:15]=2)[CH:7]=[CH:6][C:5]=1[C:8](=[O:10])[CH3:9]

Komponenten

7

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27339602-Thiopheneboronic acidHCID 220255511-(4-Iodo-2-methoxyphenyl)ethanone

Produkt 1

HCID 219810692'-Methoxy-4'-(thien-2-yl)acetophenoneAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

Ex-57a: 4′-iodo-2′-methoxyacetophenone (1.08 g, 3.9 mmol) in ethylene glycol dimethyl ether (50 ml) was degassed for 15 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.456 g, 0.39 mmol), thiophene-2-boronic acid (0.75 g, 5.9 mmol), and sodium carbonate solution (2 m, 4 ml, 8 mmol) were added. The mixture was stirred at reflux under nitrogen for 24 hours. Upon cooling to room temperature, it was poured into water and extracted with dichloromethane. The organic phase was dried over sodium sulfate and evaporated. Silica gel chromatography (hexane/ethyl acetate, 3:1) gave 0.88 g (98%) of the desired 2′-methoxy-4′-(thien-2-yl)acetophenone.

Aufarbeitung

  1. temperatureat reflux under nitrogen for 24 hours
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-754c7a9dc18444ce999681af4bf22fa9
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07078431B2

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