Water ethylacetate → 5-[3-(4-Fluoro-phenyl)-5-formyl-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid ethyl ester

HRID 1962986Notes

Reaction equation

HRID 1962986 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[C:15]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[N:16][O:17][C:18]=2/[CH:19]=C/C2C=CC=CC=2)=[CH:8][N:7]=1)=[O:5])[CH3:2].I([O-])(=O)(=O)=[O:35].[Na+].C(OCC)(=O)C.O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[C:15]([C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)=[N:16][O:17][C:18]=2[CH:19]=[O:35])=[CH:8][N:7]=1)=[O:5])[CH3:2]

Participants

8

Reactant 3

HCID 22728543Water ethylacetateHCID 23667635Sodium periodateHCID 666444395-[3-(4-Fluoro-phenyl)-5-((E)-styryl)-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 866472865-[3-(4-Fluoro-phenyl)-5-formyl-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid ethyl esterYield 72%

Reagents, catalysts & solvents 4

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

Procedure

A mixture of 5-[3-(4-fluoro-phenyl)-5-((E)-styryl)-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid ethyl ester (2.0 g, 4.5 mmol), osmium(VIII) oxide (28.6 mg, 0.11 mmol), sodium metaperiodate (3.85 g, 18 mmol), benzyltriethylammonium chloride (418 mg, 1.8 mmol) in dioxane (30 mL) and water (10 mL) was irradiated in the microwave for 15 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=4:1 to 1:1) afforded the title compound (1.2 g, 72%) as a colourless gum. MS: m/e=371.1 [M+H]+.

Workup

  1. customwas irradiated in the microwave for 15 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=4:1 to 1:1)

Sources & evidence

ORD record
ord-52e6c413ae234b8ba4622675bb79422a
Source dataset
uspto-grants-2013_04
Patent number
US08415379B2

Reaction notes

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