Phenylacetylene → HCID 54568033, compound

HRID 1596721Notes

Reaction equation

HRID 1596721 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7](OS(C(F)(F)F)(=O)=O)=[C:8]([CH:18]=1)[O:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])(=[O:3])[CH3:2].[C:27]1([C:33]#[CH:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:34]#[C:33][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:8]([CH:18]=1)[O:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 10821PhenylacetyleneHCID 10668535HCID 10668535, compound

Product 1

HCID 54568033HCID 54568033, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

A solution of t-butyl { 5-acetyl-2[(trifluoromethyl)sulfonyloxy]-phenoxy}acetate(1.0 g, 1.3 mmol) and phenylacetylene (0.33 mL, 3.0 mmol) in 20 mL triethylamine in a thick walled pyrex tube is degassed with nitrogen for 15 minutes. Bis(triphenylphosphine)-palladium(II) chloride (35 mg, 0.05 mmol) and copper (I) iodide (10 mg, 0.05 mmol) are added, and the vessel is sealed, and heated to 60° for 18 hours. After cooling, the triethylamine is removed in vacuo, and the residue is dissolved in ether (100 mL) and washed with 1 N HCl (1×100 mL) and brine (1×50 mL), dried over MgSO4, and concentrated in vacuo. Chromatography (silica, 5:1 hexane/EtOAc) yields t-butyl [5-acetyl-2-(2-phenylethynyl)-phenoxy]-acetate, along with 10% starting material. This mixture is carried on to the next step.

Workup

  1. customthe vessel is sealed
  2. temperatureheated to 60° for 18 hours
  3. temperatureAfter cooling
  4. customthe triethylamine is removed in vacuo
  5. dissolutionthe residue is dissolved in ether (100 mL)
  6. washwashed with 1 N HCl (1×100 mL) and brine (1×50 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ee3052ab2bc44d9fbe10f3d84533695b
Source dataset
uspto-grants-2001_09
Patent number
US06291530B1

Reaction notes

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