4-Fluoroanisole → (2-Fluoro-5-methoxy-phenyl)-4-pyridylmethanol

HRID 273735

Reaktionsgleichung

C([Li])CCC.CN(C)CCN(C)CCN(C)C.[F:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1.[N:27]1[CH:32]=[CH:31][C:30]([CH:33]=[O:34])=[CH:29][CH:28]=1>C1COCC1>[F:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=1[CH:33]([C:30]1[CH:31]=[CH:32][N:27]=[CH:28][CH:29]=1)[OH:34]

Komponenten

Reaktionsbedingungen

Temperatur: -75 °C

Versuchsvorschrift

Butyl lithium (47.5 ml of 2.22M solution, 105.6 mmole) was added slowly to a solution of pentamethyldiethylenetriamine (15 ml) and 4-fluoroanisole (12.61 g, 0.1 mole) in THF (150 ml) at -70° C. The solution was stirred for 2 hr at -75° C. and a solution of pyridine-4-aldehyde (9.55 ml, 0.1 mole) in THF was added at -75° C. The mixture was allowed to warm to 25° C. slowly and then quenched with ammonium chloride solution. The mixture was diluted with ethyl acetate and the organic layer was separated. The organic layer was washed with water and 3N hydrochloric acid. The acid washes were then basified with sodium hydroxide and extracted with ether and the ether solution concentrated in vacuo. The crude product was recrystallized from 80% ethanol to give (2-fluoro-5-methoxy-phenyl)-4-pyridylmethanol as a white powder (12.22 g+3.12 g second crop, 65.8% total yield).

Aufarbeitung

temperatureto warm to 25° C. slowly
customquenched with ammonium chloride solution
additionThe mixture was diluted with ethyl acetate
customthe organic layer was separated
washThe organic layer was washed with water and 3N hydrochloric acid
extractionextracted with ether
concentrationthe ether solution concentrated in vacuo
customThe crude product was recrystallized from 80% ethanol
customto give

Quellen und Nachweise

ORD-Eintrag: ord-9e5b4049d4ec4d8581fdf77a8058c374
Quelldatensatz: uspto-grants-1995_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05387593

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