Diethyl Carbonate → 4-Ethyl-4-hydroxymethyl-2-oxazolidinone

HRID 398813

Reaction equation

HRID 398813 reaction equation
[NH2:1][C:2]([CH2:7][CH3:8])([CH2:5][OH:6])[CH2:3][OH:4].[C:9](=O)(OCC)[O:10]CC>C[O-].[Na+].CCO>[CH2:7]([C:2]1([CH2:5][OH:6])[CH2:3][O:4][C:9](=[O:10])[NH:1]1)[CH3:8]

Participants

5

Reactant 2

HCID 7766Diethyl CarbonateHCID 82822-Amino-2-ethyl-1,3-propanediol

Product 1

HCID 112635594-Ethyl-4-hydroxymethyl-2-oxazolidinoneYield 66.5%

Reagents, catalysts & solvents 2

HCID 10942334Sodium MethoxideCatalystHCID 702EthanolSolvent

Procedure

Sodium methoxide (2.2 g, Aldrich) was added to a solution of 2-amino-2-ethyl-1,3-propanediol(100.0 g, Aldrich) and diethyl carbonate (169.0 g, Aldrich) This solution was refluxed in a Dean Stark apparatus until no more EtOH was collected. The reaction mixture was cooled, added acetone(200 ml) and allowed to stand overnite at room temperature. The resulting suspension was filtered to give 81.0 g of the desired product as a beige solid. 1H NMR consistent with the proposed structure.

Workup

  1. customwas collected
  2. temperatureThe reaction mixture was cooled
  3. additionadded acetone(200 ml)
  4. customto stand overnite at room temperature
  5. filtrationThe resulting suspension was filtered

Sources & evidence

ORD record
ord-58e4b581318740f5b42cfeb857ddca99
Source dataset
uspto-grants-1998_10
Patent number
US05817652

Linked notes

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