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Water ethylacetate → 6-(5-Formyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-nicotinonitrile

HRID 1514728
Notes
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Reaction equation

HRID 1514728 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:11]([CH2:12][O:13][C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=2)=[C:10](/[CH:22]=C/C2C=CC=CC=2)[O:9][N:8]=1.I([O-])(=O)(=O)=[O:31].[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>[CH:22]([C:10]1[O:9][N:8]=[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[C:11]=1[CH2:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=1)=[O:31]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 3

HCID 22728543Water ethylacetateHCID 23667635Sodium periodateHCID 667182056-[3-Pyridin-2-yl-5-([E]-styryl)-isoxazol-4-ylmethoxy]-nicotinonitrile

Product 1

HCID 866462576-(5-Formyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-nicotinonitrileYield 51%

Reagents, catalysts & solvents 5

HCID 30318
Osmium Tetroxide
Catalyst
HCID 66133Benzyl triethylammonium chlorideCatalyst
HCID 962WaterSolvent
HCID 6386tert-ButanolSolvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 6-[3-pyridin-2-yl-5-((E)-styryl)-isoxazol-4-ylmethoxy]-nicotinonitrile (0.57 g, 2 mmol), osmium(VIII) oxide solution (0.38 mL of a 2.5% solution in tert-butanol, 0.04 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 heated in a microwave for 45 min at 120° C. Extractive workup (ethyl acetate/water) was followed by drying of the organic phase over sodium sulfate and filtering. The solvent was evaporated and the residue was triturated with diisopropylether to afford the title compound (0.23 g, 51%) as a white solid. MS: m/e=307.2 [M+H]+.

Workup

  1. dry with materialby drying of the organic phase over sodium sulfate
  2. filtrationfiltering
  3. customThe solvent was evaporated
  4. customthe residue was triturated with diisopropylether

Sources & evidence

ORD record
ord-d48c01973882400b9972a5ba40cc42b9
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08222246B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes