Acetonitrile → ((4-(Benzyloxy)phenyl)ethynyl)trimethylsilane

HRID 2243566Notes

Reaction equation

HRID 2243566 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](I)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(#N)C.[CH3:19][Si:20]([C:23]#[CH:24])([CH3:22])[CH3:21]>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.C(N(CC)CC)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:24]#[C:23][Si:20]([CH3:22])([CH3:21])[CH3:19])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 6342AcetonitrileHCID 66111TrimethylsilylacetyleneHCID 5196711-(Benzyloxy)-4-iodobenzene

Product 1

HCID 58608141((4-(Benzyloxy)phenyl)ethynyl)trimethylsilane

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

A resealable tube was charged with 1-benzyloxy-4-iodobenzene 100 (5.00 g, 16.1 mmol), acetonitrile (80 mL), and triethylamine (10 mL). Dichlorobis(triphenylphosphine)palladium (II) (0.733 g, 1.05 mmol), copper (I) iodide (0.200 g, 1.05 mmol), and (trimethylsilyl)acetylene (2.06 g, 2.96 mL, 20.9 mmol) were added. The system was purged with argon, the tube was sealed, and the mixture stirred at 60° C. for 17 h. The reaction mixture was filtered twice through a pad of Celite along with ethyl acetate. The filtrate was concentrated to afford (4-benzyloxy-phenylethynyl)trimethylsilane (101) as an orange brown solid which was used without purification.

Workup

  1. customThe system was purged with argon
  2. customthe tube was sealed
  3. filtrationThe reaction mixture was filtered twice through a pad of Celite along with ethyl acetate
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-16664295c5b740278ef35a85ff31ec87
Source dataset
uspto-grants-2010_03
Patent number
US07674907B2

Reaction notes

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