[CH2:1]1COCC1.[OH:6]/[N:7]=[C:8](\[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20])/[C:9]([O:11][CH2:12][CH3:13])=[O:10].[H-].[Na+].S(OC)(OC)(=O)=O>C(OCC)(=O)C.O>[CH3:1][O:6]/[N:7]=[C:8](\[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20])/[C:9]([O:11][CH2:12][CH3:13])=[O:10]To 50 ml of a THF solution with 10.0 g of ethyl (E)-α-hydroxyimino-o-tolylacetate (48 mmol), 2.2 g of 60%-sodium hydride (53 mmol) was added under ice-cooling and the solution was stirred for 30 minutes. The solution, to which 6.7 g of dimethyl sulfate (53 mmol) was added dropwise, was stirred at room temperature for one more hour. Water and ethyl acetate were added to the reaction solution, and the organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated to give 10.4 g of ethyl (E)-α-methoxyimino-o-tolylacetate (yield; 98%).
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