Trimethylsilylacetylene → HCID 22119685, compound

HRID 725171Notes

Reaction equation

HRID 725171 reaction equation
[CH3:1][Si:2]([CH3:17])([CH3:16])[O:3][CH2:4][CH2:5][N:6]([CH2:14][CH3:15])[C:7]1[CH:12]=[CH:11][C:10](I)=[CH:9][CH:8]=1.[CH3:18][Si:19]([C:22]#[CH:23])([CH3:21])[CH3:20]>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.C(N(CC)CC)C>[CH3:1][Si:2]([CH3:17])([CH3:16])[O:3][CH2:4][CH2:5][N:6]([CH2:14][CH3:15])[C:7]1[CH:12]=[CH:11][C:10]([C:23]#[C:22][Si:19]([CH3:21])([CH3:20])[CH3:18])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 22119680HCID 22119680, compound

Product 1

HCID 22119685HCID 22119685, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture containing 10.9 g, that is 30 mmole, 4-[(2-trimethylsiloxyethyl)ethylamino]iodobenzene from the previous step, 1.0 g, that is 1.4 mmole bis(triphenylphosphine)palladium(II) chloride from Aldrich Chemical Co., and 74 mg, that is 0.75 mmole cuprous chloride, from Aldrich Chemical Co. in 50 m triethylamine was stirred and degassed under nitrogen for 15 minutes. Next 3.5 g, that is, 36 mmole trimethylsilylacetylene from Aldrich chemical Co. was added with vigorous mechanical stirring at room temperature and the final mixture was stirred at 80° C. for 1 hour. The cooled reaction mixture was filtered, diluted with ethyl ether and extracted with dilute HCL. The organic phase was separated, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The dark residue was flash column chromatographed on silica gel with 4% ethyl acetate-hexane to give 9.2 g of yellow oil at a 92% yield.

Workup

  1. additionA mixture containing 10.9 g, that
  2. customdegassed under nitrogen for 15 minutes
  3. additionwas added with vigorous
  4. customThe cooled reaction mixture
  5. filtrationwas filtered
  6. additiondiluted with ethyl ether
  7. extractionextracted with dilute HCL
  8. customThe organic phase was separated
  9. dry with materialdried over anhydrous sodium sulfate
  10. customthe solvent was removed under reduced pressure
  11. customchromatographed on silica gel with 4% ethyl acetate-hexane

Sources & evidence

ORD record
ord-75b7a6faf47943c1884754033568745c
Source dataset
uspto-grants-1998_01
Patent number
US05705570

Reaction notes

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