Nitrogen → Methyl 2-(acetoxymethyl)oxazole-4-carboxylate
Reaction equation
N#N.Cl[CH2:4][C:5]1[O:6][CH:7]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[N:9]=1.[C:14]([O:17]C(=O)C)(=[O:16])[CH3:15].C([O-])(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C.CC(=O)OCC>[C:14]([O:17][CH2:4][C:5]1[O:6][CH:7]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[N:9]=1)(=[O:16])[CH3:15]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 120 °C
Procedure
In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of methyl 2-(chloromethyl)oxazole-4-carboxylate (Organic Process Research & Development 2001, 5, 37-44) (20.00 g, 113.91 mmol) in acetic acid (80 mL) was treated with acetic anhydride (8.0 mL) followed by sodium acetate (39.72 g, 484.14 mmol). The reaction mixture was stirred at 120° C. for 3 h. EA (400 mL) was added at rt and the suspension was neutralized with sat. aq. sodium carbonate. The layers were separated and the aq. layer was extracted with EA (2×400 mL). The combined org. layers were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a white solid. LC-MS-conditions 06: tR=0.48 min, [M+H]+=200.41.
Workup
- customThe layers were separated
- extractionthe aq. layer was extracted with EA (2×400 mL)
- dry with materiallayers were dried over Na2SO4
- filtrationfiltered
- customthe solvents were removed under reduced pressure
Sources & evidence
- ORD record
- ord-5306f5a1f6594b10821c8b1cd757ab18
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846733B2
Reaction notes
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