Trimethylsilylacetylene → HCID 22119685, compound

HRID 1274047Notes

Reaction equation

HRID 1274047 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-687eeadfc8d84df8a571f19ae1009543
Source dataset
uspto-grants-2000_12
Patent number
US06156445

Reaction notes

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