Hydrochloric Acid → 4-(2-Oxo-2-pyridin-2-ylethyl)benzenecarboxylic acid

HRID 230790Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 230790
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][CH:15]=1.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29](OC)=[O:30].Cl>O.C1COCC1.CCCCCC>[O:30]=[C:29]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][N:23]=1)[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][CH:15]=1

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 7470P-Toluic AcidHCID 7912DiisopropylamineHCID 755692-CarbomethoxypyridineHCID 178418339Butyllithium

Produkt 1

HCID 690048824-(2-Oxo-2-pyridin-2-ylethyl)benzenecarboxylic acidAusbeute 11,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A THF solution (50 mL) of diisopropylamine (12.6 mL) was cooled to 0° C., and a hexane (33 mL) solution of 2.6 M n-butyllithium was added thereto and stirred at that temperature for 10 minutes. Then this was cooled to −78° C., and a THF solution (15 mL) of 4-methylbenzenecarboxylic acid (2.3 g) was dropwise added thereto. The reaction liquid was stirred at −40° C. for 2.5 hours, and then a THF solution (4 mL) of methyl picolinate (2.0 g) was dropwise added thereto. The reaction solution was heated up to room temperature, and stirred for one day. Next, water was added to the reaction liquid, then controlled to have a pH of 4 with aqueous hydrochloric acid solution added thereto, and then extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate, concentrated under reduced pressure, and the resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=4/1) to obtain the entitled compound (400 mg).

Aufarbeitung

  1. customThe reaction liquid
  2. stirringwas stirred at −40° C. for 2.5 hours
  3. temperatureThe reaction solution was heated up to room temperature
  4. stirringstirred for one day
  5. additionadded
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customthe resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=4/1)

Quellen und Nachweise

ORD-Eintrag
ord-8df35751d93e4b309d88ce135b230de5
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566781B2

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