Triethylamine → HCID 18182420, compound

HRID 1359405Notes

Reaction equation

HRID 1359405 reaction equation
FC(F)(F)S(O[C:7]1[CH:11]=[CH:10][S:9][C:8]=1[C:12]([O:14][CH3:15])=[O:13])(=O)=O.[CH3:18][Si:19]([C:22]#[CH:23])([CH3:21])[CH3:20].C(N(CC)CC)C>CN(C)C=O>[CH3:15][O:14][C:12]([C:8]1[S:9][CH:10]=[CH:11][C:7]=1[C:23]#[C:22][Si:19]([CH3:21])([CH3:20])[CH3:18])=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 11737832HCID 11737832, compound

Product 1

HCID 18182420HCID 18182420, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 2.07 g of 2-methoxycarbonyl-3-thienyl trifluoromethane sulfonate, 2.02 ml of trimethylsilylacetylene, 1.57 g of tetrakis (triphenylphosphine)palladium(0), 272 mg of cuprous iodide, 2.98 ml of triethylamine and 30 ml of N,N-dimethylformamide was stirred at 65° C. for 3 hours in a nitrogen atmosphere. Silica gel was added to the reaction solution, and the solvent was removed. The residue was subjected to silica gel column chromatography using 6% ethyl acetate/hexane, to give 1.78 g of the target compound.

Workup

  1. additionSilica gel was added to the reaction solution
  2. customthe solvent was removed

Sources & evidence

ORD record
ord-e7b9e52f0031401d940afd0548aebe0b
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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