Water → HCID 53967011, compound

1.78 g of O-methylhydroxylamine hydrochloride were added to a solution of the 3.05 g of 2'-chloro-2-t-butyldimethyl silyloxyacetophenone prepared above in a mixture of methanol, water and 1,4-dioxane. The resulting mixture was stirred at room temperature for 14 hours, and the reaction mixture was then poured into water and extracted three times with 50 ml portions of ethyl acetate. The combined extracts were washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, the solvent was distilled off, and the residue was purified by column chromatography through silica gel, eluted with a stepwise gradient of ethyl acetate (10-40%) in hexane, to give 691 mg (32.4% yield) of the less polar isomer of 2'-chloro-2-hydroxyacetophenone O-methyloxime compound and 370 mg (17.3% yield) of the more polar isomer of the title compound.

1. extractionextracted three times with 50 ml portions of ethyl acetate
2. washThe combined extracts were washed with a saturated aqueous solution of sodium chloride
3. dry with materialdried over anhydrous magnesium sulfate
4. distillationthe solvent was distilled off
5. customthe residue was purified by column chromatography through silica gel
6. washeluted with a stepwise gradient of ethyl acetate (10-40%) in hexane

ORD record

ord-0f7d49d9f9ef439b9db3e98aa27648af

Source dataset

uspto-grants-1997_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05614470