Triethylamine → 1-Phenyl-2-(trimethylsilyl)acetylene

HRID 2222119Notes

Reaction equation

HRID 2222119 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][Si:9]([C:12]#[CH:13])([CH3:11])[CH3:10].C(N(CC)CC)C>COCCOC.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>[CH3:8][Si:9]([CH3:11])([CH3:10])[C:12]#[C:13][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 11575IodobenzeneHCID 66111Trimethylsilylacetylene

Product 1

HCID 1374641-Phenyl-2-(trimethylsilyl)acetylene

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of iodobenzene (1 mmole) in DME (5 mL) was treated with trimethylsilylacetylene (2 mmole), Pd(PPh3)2Cl2 (0.035 mmole), CuI (0.08 mmole) and triethylamine (4 mmole), and the resulting reaction mixture was stirred under nitrogen at room temperature for 5 h. Evaporation followed by chromatography gave 1-trimethylsilyl-2-phenylacetylene as a solid.

Workup

  1. customthe resulting reaction mixture
  2. customEvaporation

Sources & evidence

ORD record
ord-c7cf1a3618784f01aa73dc44e79603a0
Source dataset
uspto-grants-2008_05
Patent number
US07371739B2

Reaction notes

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