Sodium periodate → 6-[3-(4-Chloro-phenyl)-5-formyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester

HRID 1514695Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)=[N:14][O:15][C:16]=2/[CH:17]=C/C2C=CC=CC=2)=[N:6][CH:5]=1.I([O-])(=O)(=O)=[O:34].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)=[N:14][O:15][C:16]=2[CH:17]=[O:34])=[N:6][CH:5]=1

Participants

Conditions

Temperature: 120 °C

Procedure

6-[3-(4-Chloro-phenyl)-5-([E]-styryl)-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (6.35 g, 14.2 mmol) was treated with osmium(VIII) oxide (90.3 mg, 355 μmol), sodium metaperiodate (12.2 g, 56.8 mmol) and benzyltriethylammonium chloride (1.32 mg, 5.68 mmol) in dioxane (140 mL) and water (47 mL). The mixture was heated for 35 min at 120° C. in a microwave. Extraction with ethyl acetate/water and chromatogaphy (silica, ethyl acetate:heptane 1:9 to 1:1) afforded the title compound (3.43 g, 65%) as a white solid. MS: m/e=373.1 [M+H]+.

Workup

extractionExtraction with ethyl acetate/water and chromatogaphy (silica, ethyl acetate:heptane 1:9 to 1:1)

Sources & evidence

ORD record: ord-5f192a90ada34554a400f58e98c6c25c
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222246B2

Reaction notes

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