Triethylamine → 1-(2,4,6-Trichlorophenyl)-2-propanone O-methyloxime

A solution of O-methyl-hydroxylamine hydrochloride (0.79 g, 9.4 mmol) in methanol (20 ml) was treated with triethylamine (1.32 ml, 9.4 mmol) followed by 1-(2,4,6-trichlorophenyl)-propan-2-one (1.5 g, 6.31 mmole). The resulting mixture was stirred at 60° C. for 3 hours. The reaction mixture was quenched with water and methanol was evaporated off. The resulting aqueous medium was extracted with ethylacetate (3×50 ml). The combined organic layers were washed with brine and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure (100 mbar; 45° C.). The resulting crude mass was purified by column chromatography using 60-120μ mesh silica gel and product collected at 2% ethyl acetate in hexane as elution system to give 1-(2,4,6-Trichloro-phenyl)-propan-2-one O-methyl-oxime (1.2 g, 76%), which was taken up for further reduction.

1. customThe reaction mixture was quenched with water and methanol
2. customwas evaporated off
3. extractionThe resulting aqueous medium was extracted with ethylacetate (3×50 ml)
4. washThe combined organic layers were washed with brine
5. dry with materialdried over anhydrous Na2SO4
6. customThe solvent was evaporated under reduced pressure (100 mbar; 45° C.)
7. customThe resulting crude mass was purified by column chromatography
8. customcollected at 2% ethyl acetate in hexane as elution system

ORD-Eintrag

ord-fdfa6c25699b4fa8a85eb7bd18158c55

Quelldatensatz

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08258169B2