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

HRID 650263Notes

Reaction equation

HRID 650263 reaction equation
[NH2:1]C(OCC)=O.C[O-].[Na+].[CH3:10][O:11][CH2:12][CH:13]1[CH2:17][O:16][C:15](=O)[O:14]1>CN(C)C=O>[CH3:10][O:11][CH2:12][CH:13]1[O:14][C:15](=[O:16])[NH:1][CH2:17]1

Participants

5

Reactant 3

HCID 5641Carbamic acid, ethyl esterHCID 43844854-(Methoxymethyl)-1,3-dioxolan-2-oneHCID 10942334Sodium Methoxide

Product 1

HCID 103131495-(Methoxymethyl)oxazolidin-2-oneYield 43.3%

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 sodium methoxide (409 mg, 7.57 mmol) and 4-methoxymethyl-1,3-dioxolan-2-one (10.0 g, 75.7 mmol), in order. The mixture was stirred for 80 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 to give the subject 5-methoxymethyloxazolidin-2-one (4.3 g, yield 43.3%).

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-1a9c6bae89a34d17984ea9eb86eb1ebe
Source dataset
uspto-grants-2001_08
Patent number
US06271388B1

Reaction notes

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