Acetic Acid → 5-(Methoxymethyl)isoxazole-4-carboxylic acid
Reaction equation
[CH3:1][O:2][CH2:3][C:4]1[O:8][N:7]=[CH:6][C:5]=1[C:9]([O:11]C)=[O:10].Cl.C(O)(=O)C.O>CC(C)=O>[CH3:1][O:2][CH2:3][C:4]1[O:8][N:7]=[CH:6][C:5]=1[C:9]([OH:11])=[O:10]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Methyl 5-(methoxymethyl)isoxazole-4-carboxylate (Preparation 42, 1.8 g, 11 mmol) was stirred in a 1:1:1 mixture of concentrated hydrochloric acid (2 ml), acetic acid (2 ml) and water (2 ml) at reflux for 6 hours. Acetone (6 ml) was added and the mixture concentrated in vacuo. The solid residue was triturated with ethyl acetate and the filtrate concentrated in vacuo to afford the title compound as an off white solid (1.4 g, 85% yield).
Workup
- temperatureat reflux for 6 hours
- concentrationthe mixture concentrated in vacuo
- customThe solid residue was triturated with ethyl acetate
- concentrationthe filtrate concentrated in vacuo
Sources & evidence
- ORD record
- ord-ba0c447e30bf4982a99d930cff454302
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08134007B2
Reaction notes
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