Trimethylsilylacetylene → 2-Trimethylsilylethen-1-yl-benzoate

HRID 1168157Notes

Reaction equation

HRID 1168157 reaction equation
I[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH3:13][Si:14](C#C)([CH3:16])[CH3:15]>C(N(CC)CC)C.[Cu](I)I.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>[CH3:13][Si:14]([CH3:16])([CH3:15])[CH:10]=[CH:9][O:8][C:6](=[O:7])[C:5]1[CH:11]=[CH:12][CH:2]=[CH:3][CH:4]=1

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 142891Ethyl 4-iodobenzoate

Product 1

HCID 851768502-Trimethylsilylethen-1-yl-benzoateYield 116.9%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

A solution of ethyl 4-iodo-benzoate (55.2 g, 0.2 mol) in triethylamine (800 mL) was purged with argon. Copper iodide (1.1 g) and bis(triphenylphosphine)palladium(II) dichloride (7.0 g) were then added and the mixture was purged again. Trimethylsilylacetylene (42 mL, 0.3 mol) was then added at 0° C. for 30 minutes and the resulting mixture was stirred at room temperature for 1 hour. The mixture was concentrated, triturated in hexane and filtered. The filtrate was concentrated to give ethyl 4-(2-trimethylsilylethen-1-yl-benzoate (51.5 g, 100% crude) as a black oil.

Workup

  1. customthe mixture was purged again
  2. concentrationThe mixture was concentrated
  3. customtriturated in hexane
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-34d2d09967c247a8bd1ba9e26488fd31
Source dataset
uspto-grants-2003_09
Patent number
US06624154B1

Reaction notes

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