1,4-Dioxane → HCID 22221246, compound

HRID 1794347Notes

Reaction equation

HRID 1794347 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[CH2:13][CH2:14][CH2:15][OH:16])=[CH:4][CH:3]=1.[Cu](C#N)[C:18]#[N:19].O1CCOCC1>[C-]#N.C([N+](CC)(CC)CC)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O>[C:18]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[CH2:13][CH2:14][CH2:15][OH:16])=[CH:4][CH:3]=1)#[N:19]

Participants

8

Reactant 3

HCID 312751,4-DioxaneHCID 22221424HCID 22221424, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 22221246HCID 22221246, compoundYield 52%

Reagents, catalysts & solvents 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 3014735Tetraethylammonium cyanideCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 3-[5-(4-bromophenyl)-4-isoxazolyl]propan-1-ol (1.10 g), copper cyanide (1.41 g), tris(dibenzylideneacetone)dipalladium (130 mg), 1,1′-bis(diphenylphosphino)ferrocene (314 mg), tetraethylammonium cyanide (553 mg) and 1,4-dioxane (20 ml) was refluxed for 3.5 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and 3-[5-(4-cyanophenyl)-4-isoxazolyl]propan-1-ol (418 mg, yield 52%) was obtained as pale yellow crystals from a fraction eluted with ethyl acetate-hexane (1:3, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point: 82–83° C.

Workup

  1. temperaturewas refluxed for 3.5 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-165c79cfd5cc4f1fab6ce668d652baed
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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