Dimethyl Sulfate → HCID 10867846, compound

HRID 1738604Notes

Reaction equation

HRID 1738604 reaction equation
[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]

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 140402281HCID 140402281, compound

Product 1

HCID 10867846HCID 10867846, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

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%).

Workup

  1. temperaturecooling
  2. stirringwas stirred at room temperature for one more hour
  3. washthe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-14da886a4a4040b98523931146f7af3d
Source dataset
uspto-grants-1999_10
Patent number
US05962723

Reaction notes

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