Trimethylsilylacetylene → HCID 20083254, compound

HRID 1608943Notes

Reaction equation

HRID 1608943 reaction equation
[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][C:8](Br)=[CH:9][CH:10]=2)[S:5][C:4](=[O:13])[CH2:3]1.[CH3:15][Si:16]([C:19]#[CH:20])([CH3:18])[CH3:17]>C(N(CC)CC)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][C:8]([C:20]#[C:19][Si:16]([CH3:18])([CH3:17])[CH3:15])=[CH:9][CH:10]=2)[S:5][C:4](=[O:13])[CH2:3]1

Participants

5

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 20083246HCID 20083246, compound

Product 1

HCID 20083254HCID 20083254, compound

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
55 °C

Procedure

A solution of 1.0 g (3.7 mmol) of 4,4-dimethyl-7-bromo-2-oxo-thiochroman in 1 ml of triethylamine was placed in a heavy-walled tube and degassed and then treated under argon with 2.0 g (2.75 ml, 20.0 mmol) of trimethylsilylacetylene and a powdered mixture of 0.038 g of cuprous iodide and 0.084 g of bis(triphenylphosphine) palladium (II) chloride. The reaction mixture was degassed again, then placed under argon and the tube was sealed. The mixture was heated at 55 degrees C. for 24 hours, and thereafter allowed to cool to room temperature. Solvent was removed in-vacuo to give the title compound as a yellow oil.

Workup

  1. customdegassed
  2. customThe reaction mixture was degassed again
  3. customthe tube was sealed
  4. temperatureto cool to room temperature
  5. customSolvent was removed in-vacuo

Sources & evidence

ORD record
ord-cd08a32c15a446b39b062e4b93a1daf8
Source dataset
uspto-grants-1995_03
Patent number
US05399561

Reaction notes

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