Trimethylsilylacetylene → HCID 20083242, compound

HRID 1608942Notes

Reaction equation

HRID 1608942 reaction equation
[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][CH:8]=[C:9](Br)[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][CH:8]=[C:9]([C:20]#[C:19][Si:16]([CH3:18])([CH3:17])[CH3:15])[CH:10]=2)[S:5][C:4](=[O:13])[CH2:3]1

Participants

5

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 156611194,4-Dimethyl-6-bromo-2-oxo-thiochroman

Product 1

HCID 20083242HCID 20083242, 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-6-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, allowed to cool to room temperature and taken up with methylene chloride and silica. Solvent was removed in-vacuo and the resulting residual material on silica was purified using flash chromatography (SiO2 ; 2% ethyl acetate in hexanes) 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
  6. customthe resulting residual material on silica was purified

Sources & evidence

ORD record
ord-e3193db13dbf43269977d400868b6abc
Source dataset
uspto-grants-1995_03
Patent number
US05399561

Reaction notes

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