Benzoic acid, 3-methyl-, methyl ester → 1-(2-Methylphenyl)-2-(4-pyridyl)ethanone

HRID 1251567Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1251567
C[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7]C)=O.[N:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1.[CH3:19][Si]([N-][Si](C)(C)C)(C)C.[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1>[C:3]1([CH3:19])[CH:2]=[CH:11][CH:10]=[CH:9][C:4]=1[C:5](=[O:7])[CH2:18][C:15]1[CH:16]=[CH:17][N:12]=[CH:13][CH:14]=1

Komponenten

6

Edukt 4

HCID 7435Benzoic acid, 3-methyl-, methyl esterHCID 79634-MethylpyridineHCID 516892Sodium BicarbonateHCID 2724254Sodium bis(trimethylsilyl)amide

Produkt 1

HCID 114357761-(2-Methylphenyl)-2-(4-pyridyl)ethanoneAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Methyl 3-methylbenzoate (6.0 g, 40 mmol), tetrahydrofuran (50 mL), and 4-picoline (4.1 g, 44 mmol) were stirred at −78° C. under an atmosphere of nitrogen. Sodium bis(trimethylsilyl)amide 1.0 M in THF (88 mL, 88 mmol) was added dropwise. The mixture was allowed to warm to room temperature and stir for 16 h when it was poured into saturated aqueous sodium bicarbonate solution. The mixture was then extracted with ethyl acetate (3×50 mL). The combined organics were washed with brine (2×50 mL), dried over magnesium sulfate, and concentrated. The product was recrystallized from ethyl acetate/hexane to yield a light yellow solid (5.7 g, 67%): mp 118.0-119.0° C. 1H NMR (acetone-d6/300 MHz) 8.50 (m, 2H), 7.90 (m, 2H), 7.44 (m, 2H), 7.29 (m, 2H), 4.45 (s, 2H), 2.41 (s, 3H). ESHRMS m/z 212.1067 (M+H, C14H13NO requires 212.1075).

Aufarbeitung

  1. extractionThe mixture was then extracted with ethyl acetate (3×50 mL)
  2. washThe combined organics were washed with brine (2×50 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe product was recrystallized from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-a2e90cb1b7a84a0caec04b6602d3abe3
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06342608B1

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