Ethyl anisate → 2-(6-Chloro-2-pyridinyl)-1-(4-methoxyphenyl)ethanone

HRID 896773

Reaktionsgleichung

[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:21]=[CH:20][C:14]([C:15](OCC)=[O:16])=[CH:13][CH:12]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>O1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][C:15]([C:14]2[CH:20]=[CH:21][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)=[O:16])[CH:5]=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 45 °C

Versuchsvorschrift

To a cold (0° C.) solution of 6-chloro-2-picoline (18.3 mL, 166.5 mmol) and ethyl 4-methoxybenzoate (30.0 g, 166.5 mmol) in tetrahydrofuran (300 mL) was added lithium bis(trimethylsilyl)amide (333 mL 1.0 M in tetrahydrofuran, 332.7 mmol) dropwise via a pressure equalizing funnel over 1 hour. Upon complete addition, the cold bath was removed and the resulting solution was heated at 45° C. for 15 hours. The mixture was cooled to room temperature, and the solution was concentrated. Methanol was added to quench the reaction, resulting in the formation of a yellow precipitate. The precipitate was collected by filtration and dried to give 2-(6-chloro-2-pyridinyl)-1-(4-methoxyphenyl)ethanone (37.4 g, 86%) as a yellow solid. 1H NMR (CDCl3): δ 7.99 (d, 2H), 7.57 (t, 1H), 7.22-7.19 (m, 2H), 6.90 (d, 2H), 4.39 (s, 2H), 3.83 (s, 3H); MS m/z 262 (M+1).

Aufarbeitung

customover 1 hour
additionUpon complete addition
customthe cold bath was removed
temperatureThe mixture was cooled to room temperature
concentrationthe solution was concentrated
additionMethanol was added
customto quench
customthe reaction
customresulting in the formation of a yellow precipitate
filtrationThe precipitate was collected by filtration
customdried

Quellen und Nachweise

ORD-Eintrag: ord-7aea7040cc2c49398a3d5db98efaf431
Quelldatensatz: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06919352B2

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