Reaction #948

Reaction equation

2-amino-2-ethyl-1,3-propanediol

diethyl carbonate

EtOH

→

desired product

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

Conditions

Workup

1. 1
   Otherwas collected
2. 2
   TemperatureThe reaction mixture was cooled
3. 3
   workup.ADDITIONadded acetone (200 ml)
4. 4
   Otherto stand overnite at room temperature
5. 5
   FiltrationThe resulting suspension was filtered

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.

Source