4-Hydroxybenzaldehyde → 4-(Pyridin-2-ylmethoxy)benzaldehyde

HRID 1056815

Reaktionsgleichung

[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl.Cl[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1>CN(C)C=O.C(OCC)(=O)C>[N:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

In 5.0 mL of N,N-dimethylformamide was dissolved 611 mg (5.00 mmol) of 4-hydroxybenzaldehyde. To this solution were added 3.26 g (10.0 mol) of cesium carbonate and 0.98 g (6.0 mmol) of 2-chloromethylpyridine hydrochloride at room temperature and the mixture was stirred at 50° C. overnight. The resulting reaction mixture was diluted with ethyl acetate (100 mL), washed with water and then with saturated brine (each in an amount of 30 mL), and dried over magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20 to 50/50) to give 821 mg (77% yield) of the title compound as a light green crystal.

Aufarbeitung

customThe resulting reaction mixture
washwashed with water
dry with materialwith saturated brine (each in an amount of 30 mL), and dried over magnesium sulfate
filtrationAfter filtration
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20 to 50/50)

Quellen und Nachweise

ORD-Eintrag: ord-aa1cce5f5f384bfcbc6d3037a277e167
Quelldatensatz: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09399635B2

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