Carbamic acid, ethyl ester → 5-(Methoxymethyl)oxazolidin-2-one
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]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- filtrationAfter filtering off the insoluble materials
- customcondensed in vacuo
- 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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