Trimethylsilylacetylene → HCID 58074417, compound

HRID 2366354Notes

Reaction equation

HRID 2366354 reaction equation
[C:1]([Si:3]([CH3:6])([CH3:5])[CH3:4])#[CH:2].Br[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][O:16][CH3:17])=[CH:10][CH:9]=1>N1CCCCC1.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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:17][O:16][CH2:15][CH2:14][C:11]1[CH:12]=[CH:13][C:8]([C:2]#[C:1][Si:3]([CH3:6])([CH3:5])[CH3:4])=[CH:9][CH:10]=1

Participants

7

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 219957171-Bromo-4-(2-methoxyethyl)benzene

Product 1

HCID 58074417HCID 58074417, compoundYield 80.7%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8082PiperidineSolvent

Conditions

Temperature
100 °C

Procedure

Ethynyltrimethylsilane (3.42 g, 34.9 mmol) was added via syringe to a mixture of 1-bromo-4-(2-methoxyethyl)benzene (5 g, 23.25 mmol), bis(triphenylphosphine)palladium dichloride (0.326 g, 0.465 mmol), triphenylphosphine (0.305 g, 1.162 mmol) and copper(I) iodide (0.089 g, 0.465 mmol) in piperidine (25 mL). The mixture was heated to 100° C. for 1 h under a nitrogen atmosphere, then cooled and concentrated under vacuum. The residue was taken up in ethyl acetate (70 mL), filtered and concentrated to give the crude product that was then purified by flash chromatography on silica gel (ISCO 120 g column, 0-20% ethyl acetate in n-heptane as the eluent). Product (4.36 g) was obtained as a brown oil (MS: (M+H)+=233.3).

Workup

  1. temperaturecooled
  2. concentrationconcentrated under vacuum
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude product that
  6. customwas then purified by flash chromatography on silica gel (ISCO 120 g column, 0-20% ethyl acetate in n-heptane as the eluent)

Sources & evidence

ORD record
ord-1f301de384c44e7f88b87fd88b98df54
Source dataset
uspto-grants-2014_04
Patent number
US08697739B2

Reaction notes

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