Water ethylacetate → HCID 86646253, compound

HRID 1514671Notes

Reaction equation

HRID 1514671 reaction equation
[CH3:1][O:2][C:3](=[O:31])[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][CH:28]=[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:33].[Na+].C(OCC)(=O)C.O>C(O)(C)(C)C.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[CH3:1][O:2][C:3](=[O:31])[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][CH:28]=[CH:27][CH:26]=3)=[N:14][O:15][C:16]=2[CH:17]=[O:33])=[N:6][CH:5]=1

Participants

9

Reactant 3

HCID 22728543Water ethylacetateHCID 23667635Sodium periodateHCID 66718199HCID 66718199, compound

Product 1

HCID 86646253HCID 86646253, compoundYield 51.2%

Reagents, catalysts & solvents 5

HCID 30318Osmium TetroxideCatalystHCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6-[3-phenyl-5-((E)-styryl)-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (0.62 g, 1.5 mmol), osmium(VIII) oxide solution (0.38 mL of a 2.5% solution in tert-butanol, 0.037 mmol), sodium metaperiodate (1.29 g, 6 mmol), benzyltriethylammonium chloride (0.14 g, 0.6 mmol) in dioxane (13 mL) and water (4.5 mL) was irradiated in the microwave for 10 min at 120° C. Extractive workup (ethyl acetate/water) was followed by drying of the organic phase over sodium sulfate, filtered and concentrated. Purification by chromatography (silica, heptane:ethyl acetate=100:0 to 60:40) afforded the title compound as a light yellow solid (0.26 g, 51%). MS: m/e=339.3 [M+H]+.

Workup

  1. customwas irradiated in the microwave for 10 min at 120° C
  2. dry with materialby drying of the organic phase over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by chromatography (silica, heptane:ethyl acetate=100:0 to 60:40)

Sources & evidence

ORD record
ord-dea0e37dc24648799d96f5571af328be
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

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