1989
DOI: 10.1002/jhet.5570260125
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Reduction of n‐(1,3‐dioxolan‐2‐yl)‐1‐methylpyridinium ions: Molecular structure of the 4‐(l,3‐dioxolan‐2‐yl)‐1‐methyl‐1,2,3,6‐tetrahydropyridine‐borane complex

Abstract: The reduction of the n‐(1,3‐dioxolan‐2‐yl)‐1‐methylpyridinium ions with sodium borohydride has been studied to prepare N‐methylformylpiperidines. Deuterium oxide was used as the solvent in order to assign the protons in the nmr spectra. As a product of the reaction, the 4‐(1,3‐dioxolan‐2‐yl)‐1‐methyl‐1,2,3,6‐tetrahy‐dropyridine‐borane complex, was isolated and crystallized. A X‐ray study of this borane complex has been carried out.

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“…The acetal was produced according to a published method (51). A stirred solution of pyridine-4-carboxaldehyde (8.7 mL, 90 mmol), ethylene glycol (10 mL, 180 mmol), and p-toluenesulfonic acid (18.8 g, 99 mmol) in benzene (70 mL) was refluxed overnight, with removal of H2O in a Dean-Stark apparatus.…”
Section: Pyridine 4-(13-dioxalan-2-yl)mentioning
confidence: 99%
“…The acetal was produced according to a published method (51). A stirred solution of pyridine-4-carboxaldehyde (8.7 mL, 90 mmol), ethylene glycol (10 mL, 180 mmol), and p-toluenesulfonic acid (18.8 g, 99 mmol) in benzene (70 mL) was refluxed overnight, with removal of H2O in a Dean-Stark apparatus.…”
Section: Pyridine 4-(13-dioxalan-2-yl)mentioning
confidence: 99%