Sodium Hydroxide → HCID 21930329, compound

HRID 1243645Notes

Reaction equation

HRID 1243645 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14](/[CH:16]=[CH:17]/[C:18]3[O:22][CH:21]=[CH:20][CH:19]=3)=O)=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.Cl.[NH2:24][OH:25].[OH-].[Na+]>>[O:22]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:17]1[O:25][N:24]=[C:14]([C:11]2[CH:12]=[CH:13][C:8]([O:7][C:4]3[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=3)=[CH:9][CH:10]=2)[CH:16]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 5761334HCID 5761334, compound

Product 1

HCID 21930329HCID 21930329, compound

Procedure

To a mixture of 3-furan-2-yl-1-(4-phenoxy-phenyl)-propenone (0.4 g, 1.4 mmol) and hydroxylamine hydrochloride (0.14 g, 2.1 mmol), was added sodium hydroxide (0.11 g, 2.8 mmol). The reaction mixture was heated to reflux for 3 days. The mixture was then concentrated, and neutralized with diluted HCl. Ethyl acetate and water were added. The organic layer was separated and dried over sodium sulfate. The solvent was removed and the residue was purified by column chromatography (silica, eluted with 20% ethyl acetate/hexanes) to give the desired isoxazole in poor yield (10 mg).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 days
  3. concentrationThe mixture was then concentrated
  4. additionEthyl acetate and water were added
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed
  8. customthe residue was purified by column chromatography (silica, eluted with 20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-375a98bbe1a1479d99ec363056a04130
Source dataset
uspto-grants-2006_10
Patent number
US07119120B2

Reaction notes

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