Trimethylsilylacetylene → 3-(4-Bromophenyl)-5-(trimethylsilyl)isoxazole

HRID 736394Notes

Reaction equation

HRID 736394 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]=[N:7][OH:8])=[CH:4][CH:3]=1.[CH3:11][Si:12]([C:15]#[CH:16])([CH3:14])[CH3:13]>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[CH:16]=[C:15]([Si:12]([CH3:14])([CH3:13])[CH3:11])[O:8][N:7]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 6080884-Bromobenzaldehyde Oxime

Product 1

HCID 221704493-(4-Bromophenyl)-5-(trimethylsilyl)isoxazole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product from Example 42A (0.124 g, 0.621 mmol) and trimethylsilylacetylene (0.35 mL, 2.5 mmol) were combined in tetrahydrofuran (2.2 mL), treated bleach (2.2 mL), and stirred for 22 hours. The mixture was diluted with ethyl acetate (7 mL), washed with brine (5 mL), dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (7% ethyl acetate in hexanes) to provide the title compound.

Workup

  1. additiontreated bleach (2.2 mL)
  2. washwashed with brine (5 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (7% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-a508347bbb9b47cdaa96cfeffd488b18
Source dataset
uspto-grants-2009_09
Patent number
US07595332B2

Reaction notes

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