Pyridine → N-methyl-N-methoxy-(E)-5-methyl-4-bis(4-fluorophenyl)methylidene-2-hexenamide

Temperatur

60 °C

To the above carboxylic acid (1.70 g, 5.2 mmol) dissolved in benzene (15 ml) was added under argon atmosphere oxalyl chloride (1.27 g, 0.87 ml, 10.0 mmol) distilled right before use. After stirring at 60° C. for 2 hours, the solvent and excess oxalyl chloride were removed by evaporation at 60° C. under 20 Torr. To the residue dissolved in dichloromethane (25 ml) were added N,O-dimethoxyhydroxylamine hydrochloride (0.52 g, 5.34 mmol) and pyridine (0.85 g, 0.86 ml, 10.7 mmol), and the whole was stirred at room temperature overnight. The mixture was diluted with diethyl ether (100 ml), and the organic layer was washed with saturated ammonium chloride aq solution (100 ml×twice), dried over anhydrous magnesium sulfate, and concentrated in vacuo. The resulting crude product was purified by column chromatography (silica gel, ethyl acetate:hexane=3:7) to give 1.62 g (82% yield) of N-methyl-N-methoxy-(E)-5-methyl-4-bis (4-fluorophenyl)methylidene-2-hexenamide. mp=109° -110° C. Rf =0.48 (hexane:ethyl acetate=2:1) IR (KBr): 3200, 3005, 2960, 1660, 1610, 1515, 1420, 1390, 1235, 1170, 1105, 1070, 1005, 865, 850, 810, 590, 575 cm-1.

1. distillationdistilled right before use
2. customthe solvent and excess oxalyl chloride were removed by evaporation at 60° C. under 20 Torr
3. dissolutionTo the residue dissolved in dichloromethane (25 ml)
4. stirringthe whole was stirred at room temperature overnight
5. washthe organic layer was washed with saturated ammonium chloride aq solution (100 ml×twice),
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationconcentrated in vacuo
8. customThe resulting crude product was purified by column chromatography (silica gel, ethyl acetate:hexane=3:7)

ORD-Eintrag

ord-b12fae66fbab4e5c80c8afbd7d881bd3

Quelldatensatz

uspto-grants-1994_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05369109