Trimethylsilylacetylene → HCID 15745229, compound

HRID 1707880Notes

Reaction equation

HRID 1707880 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9](I)=[C:8](F)[CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH3:14][Si:15]([C:18]#[CH:19])([CH3:17])[CH3:16]>C(NCC)C.[Cu]I>[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:19]#[C:18][Si:15]([CH3:17])([CH3:16])[CH3:14])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 18960147HCID 18960147, compound

Product 1

HCID 15745229HCID 15745229, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8021DiethylamineSolvent

Procedure

A mixture of 0.1 mol of 4-pentyl-2-fluoro-iodobenzene, 0.12 mol of trimethylsilylacetylene, 0.0014 mol of bis(triphenylphosphine)-palladium(II) chloride Pd(PPh3)2Cl2 and 0.7 mmol of copper (I) iodide in 250 ml diethylamine is stirred at room temperature for 20 hours. After evaporation of the solvent the crude product is purified by chromatography on alumina (4:1 petrol/difluoromethane) to give 2-(4-pentylphenyl)-1-trimethylsilylacetylene. Removal of the trimethylsilylgroup is accomplished by treatment this acetylene in methanol with 1M KOH for 1 hour at room temperature. Evaporation of the methanol and either extraction yields 4-pentyl-2-fluoro-phenylacetylene.

Workup

  1. customAfter evaporation of the solvent the crude product
  2. customis purified by chromatography on alumina (4:1 petrol/difluoromethane)

Sources & evidence

ORD record
ord-3dad28e912744b6488ddce920835fd16
Source dataset
uspto-grants-1994_10
Patent number
US05356562

Reaction notes

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