Sodium Methoxide → 4-(Methoxymethyl)-4-methyloxazolidin-2-one

HRID 539109Notes

Reaction equation

HRID 539109 reaction equation
CC1C=CC(S([O:11][CH2:12][C:13]2([CH3:19])[CH2:17][O:16][C:15](=[O:18])[NH:14]2)(=O)=O)=CC=1.[CH3:20][O-].[Na+]>CO.O>[CH3:20][O:11][CH2:12][C:13]1([CH3:19])[CH2:17][O:16][C:15](=[O:18])[NH:14]1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 57461222(4-Methyl-2-oxooxazolidin-4-yl)methyl 4-methylbenzenesulfonate

Product 1

HCID 655855284-(Methoxymethyl)-4-methyloxazolidin-2-oneYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a round bottom flask containing (4-methyl-2-oxooxazolidin-4-yl)methyl 4-methylbenzenesulfonate (300 mg, 1.05 mmol) was added under a nitrogen atmosphere 3 ml of sodium methoxide in methanol solution (25% wt). The resulting thick suspension was stirred at ambient temperature for 24 hours, and then heated at 80° C. for 18 hours. The reaction was cooled to ambient temperature, diluted with water, and the pH was adjusted to neutral. The mixture was concentrated, and the resulting solids were extracted with DCM and EtOAc. The combined organic layer was concentrated to afford 4-(methoxymethyl)-4-methyloxazolidin-2-one (129 mg, 85%) as an oil.

Workup

  1. temperatureheated at 80° C. for 18 hours
  2. temperatureThe reaction was cooled to ambient temperature
  3. concentrationThe mixture was concentrated
  4. extractionthe resulting solids were extracted with DCM and EtOAc
  5. concentrationThe combined organic layer was concentrated

Sources & evidence

ORD record
ord-9cfd8d0d48544e7cb0673e2f782cb389
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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