Hydrochloric Acid → 2-[(Trimethylsilyl)ethynyl]toluene

HRID 556333Notes

Reaction equation

HRID 556333 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8].[CH3:9][Si:10]([C:13]#[CH:14])([CH3:12])[CH3:11].Cl>C(N(CC)CC)C.[Cu]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:9][Si:10]([CH3:12])([CH3:11])[C:13]#[C:14][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 51282-IodotolueneHCID 66111Trimethylsilylacetylene

Product 1

HCID 44632812-[(Trimethylsilyl)ethynyl]tolueneYield 94.6%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8471TriethylamineSolvent

Procedure

2-Iodotoluene (81.5 ml, 0.64 mol) and trimethylsilylacetylene (99 ml, 0.71 mol) were dissolved in triethylamine (250 ml). Triphenylphosphine (0.427 g, 1.6 mmol), copper (I) iodide (0.3 g, 1.6 mmol) and bistriphenyphosphinepalladium (II) dichloride (0.53 g, 0.71 mmol) were added and the mixture was heated under reflux for 18 h. The mixture was cooled to ambient temperature and carefully added to 10% hydrochloric acid (480 ml) and the product was extracted into hexane (3×200 ml). The extracts were washed with 10% hydrochloric acid (200 ml) and water (2×200 ml) then dried (MgSO4) and evaporated in vacuo to give trimethyl-(2-methylphenyl)ethynylsilane (114.06 g) as a yellow oil, which was used without further purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 h
  3. extractionthe product was extracted into hexane (3×200 ml)
  4. washThe extracts were washed with 10% hydrochloric acid (200 ml) and water (2×200 ml)
  5. dry with materialthen dried (MgSO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-c74cd236506e4b95ac8cc2fb18b7d9aa
Source dataset
uspto-grants-2011_11
Patent number
US08058283B2

Reaction notes

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