Reacción #948

ord-70a686d8594848a0be625406e5a5cefa

Ecuación de reacción

CCC(N)(CO)CO
2-amino-2-ethyl-1,3-propanediol
CCOC(=O)OCC
diethyl carbonate
CCO
EtOH
CCN1C(=O)OCC1CO
desired product
CCN1C(=O)OCC1CO
(+-)-Ethyl-4-(hydroxymethyl)-2-oxazolidinone

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrowas collected
  2. 2
    TemperaturaThe reaction mixture was cooled
  3. 3
    workup.ADDITIONadded acetone (200 ml)
  4. 4
    Otroto stand overnite at room temperature
  5. 5
    FiltraciónThe resulting suspension was filtered

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05723458uspto-grants-1998_03