Methyl 3-hydroxyisoxazole-5-carboxylate → 3-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid methyl ester

HRID 1920898Notes

Reaction equation

HRID 1920898 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][OH:14].[CH3:15][O:16][C:17]([C:19]1[O:23][NH:22][C:21](=O)[CH:20]=1)=[O:18]>>[CH3:15][O:16][C:17]([C:19]1[O:23][N:22]=[C:21]([O:14][CH2:13][C:3]2[C:4]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[N:5][O:6][C:2]=2[CH3:1])[CH:20]=1)=[O:18]

Participants

3

Reactant 2

HCID 2724585Methyl 3-hydroxyisoxazole-5-carboxylateHCID 2776149(5-Methyl-3-phenyl-1,2-oxazol-4-yl)methanol

Product 1

HCID 674922963-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid methyl esterYield 63%

Procedure

As described for Intermediate 1, (5-methyl-3-phenyl-isoxazol-4-yl)-methanol (1.0 g, 5.3 mmol) was converted, using 3-oxo-2,3-dihydro-isoxazole-5-carboxylic acid methyl ester (756 mg, 5.3 mmol) instead of 3-hydroxy-5-methylisoxazole, to the title compound (1.04 g, 63%) which was obtained as a colourless gum after purification by chromatography (silica, heptane:ethyl acetate=4:1 to 0:1). MS: m/e=315.0 [M+H]+.

Sources & evidence

ORD record
ord-67a38da2a4bd4ca89cfb1f42eb10a575
Source dataset
uspto-grants-2012_05
Patent number
US08173652B2

Reaction notes

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