Carbamic acid, ethyl ester → 5-(Methoxymethyl)oxazolidin-2-one

HRID 650262Notes

Reaction equation

HRID 650262 reaction equation
[NH2:1]C(OCC)=O.C(=O)([O-])[O-].[K+].[K+].[CH3:13][O:14][CH2:15][CH:16]1[CH2:20][O:19][C:18](=O)[O:17]1>CN(C)C=O>[CH3:13][O:14][CH2:15][CH:16]1[O:17][C:18](=[O:19])[NH:1][CH2:20]1

Participants

5

Reactant 3

HCID 5641Carbamic acid, ethyl esterHCID 11430Potassium CarbonateHCID 43844854-(Methoxymethyl)-1,3-dioxolan-2-one

Product 1

HCID 103131495-(Methoxymethyl)oxazolidin-2-oneYield 23.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

Urethane (10.0 g, 113 mmol) was dissolved in N,N-dimethylformamide (40 ml), and thereto were added potassium carbonate (20.8 g, 151 mmol) and 4-methoxymethyl-1,3-dioxolan-2-one (10.0 g, 75.7 mmol), in order. The mixture was stirred for 100 hours at 140° C. under an atmosphere of argon. After filtering off the insoluble materials, the filtrate was condensed in vacuo, and the residue was purified by silica gel chromatography give the subject 5-methoxymethyloxazolidin-2-one (2.3g, yield 23.1%).

Workup

  1. filtrationAfter filtering off the insoluble materials
  2. customcondensed in vacuo
  3. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-3f60b4333f5b42eb821da85c3cdfd349
Source dataset
uspto-grants-2001_08
Patent number
US06271388B1

Reaction notes

Loading…