[CH3:1][C:2]1([CH3:26])[CH2:6][C:5]2[C:7]([CH3:25])=[C:8]([CH3:24])[C:9]([CH:12]3[CH2:17][C:16](=[O:18])[C:15]([C:19](=O)[CH2:20][CH3:21])=[C:14]([OH:23])[CH2:13]3)=[C:10]([CH3:11])[C:4]=2[O:3]1.C([O-])(=O)C.[Na+].Cl.[CH2:33]([O:35][NH2:36])[CH3:34]>C(O)C>[CH3:1][C:2]1([CH3:26])[CH2:6][C:5]2[C:7]([CH3:25])=[C:8]([CH3:24])[C:9]([CH:12]3[CH2:17][C:16](=[O:18])[C:15]([C:19](=[N:36][O:35][CH2:33][CH3:34])[CH2:20][CH3:21])=[C:14]([OH:23])[CH2:13]3)=[C:10]([CH3:11])[C:4]=2[O:3]1To a solution 0.3 g of the 5-(2,3-dihydro-2,2,4,5,7-pentamethylbenzofuran-6-yl)-2-propionyl-3-hydroxycyclohex-2-en-1-one in 10 ml of ethanol was added 0.14 g of sodium acetate and 0.09 g of ethoxyamine hydrochloric acid. After stirring at room temperature for 20 hours, the reaction mixture was quenched with 20 ml water and extracted with diethyl ether. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under the reduced pressure to afford a crude product. Final purification was carried by silica-gel column chromatography to afford 0.28 g of 5-(2,3-dihydro-2,2,4,5,7-pentamethylbenzofuran-6-yl)-2-[1-(ethoxyimino)propyl]-3-hydroxycyclohex-2-en-1-one as yellow oil.
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