Diethyl Ether → HCID 22727321, compound

HRID 2086391Notes

Reaction equation

HRID 2086391 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:14]=[C:13]([CH2:15][CH2:16][CH2:17][OH:18])[O:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C([O-])(=O)C.[Na+].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C(OCC)C>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:14]=[C:13]([CH2:15][CH2:16][CH:17]=[O:18])[O:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 517045Sodium AcetateHCID 22727363HCID 22727363, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 22727321HCID 22727321, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[3-(3-nitrophenyl)isoxazol-5-yl]propan-1-ol (1.02 g, 4.1 mmol), sodium acetate (0.10 g, 1.3 mmol), and pyridinium chlorochromate (1.77 g, 8.2 mmol) were added in 30 mL of dry methylene chloride. After the reaction was continued for 4 hr at an ambient temperature, diethyl ether was added and the reaction mixture was filtered through a cellite bed. 0.6 g (64%) of the target compound was obtained by removing all the solvent and purifying by column chromatography on silica gel.

Workup

  1. filtrationthe reaction mixture was filtered through a cellite bed

Sources & evidence

ORD record
ord-d1e2631907fc4fc5aec172ddbb72d69d
Source dataset
uspto-grants-2004_04
Patent number
US06723724B2

Reaction notes

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