Ethanol → (+-)-Ethyl-4-(hydroxymethyl)-2-oxazolidinone

HRID 852

Reaction equation

HRID 852 reaction equation
[NH2:1][C:2](CC)([CH2:5][OH:6])[CH2:3][OH:4].[C:9](=O)(OCC)[O:10]CC.[CH3:17][CH2:18]O>C[O-].[Na+]>[CH2:17]([N:1]1[CH:2]([CH2:3][OH:4])[CH2:5][O:6][C:9]1=[O:10])[CH3:18]

Participants

5

Reactant 3

HCID 702EthanolHCID 7766Diethyl CarbonateHCID 82822-Amino-2-ethyl-1,3-propanediol

Product 1

HCID 19694098(+-)-Ethyl-4-(hydroxymethyl)-2-oxazolidinone

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideCatalyst

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-70a686d8594848a0be625406e5a5cefa
Source dataset
uspto-grants-1998_03
Patent number
US05723458

Linked notes

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