Trimethylsilylacetylene → HCID 19992007, compound
Reaction equation
I[C:2]1[N:7]=[CH:6][C:5]([C:8]23[O:15][CH2:14][C:11]([CH2:16][CH2:17][CH3:18])([CH2:12][O:13]2)[CH2:10][O:9]3)=[CH:4][CH:3]=1.[CH3:19][Si:20]([C:23]#[CH:24])([CH3:22])[CH3:21]>C(NCC)C>[CH2:16]([C:11]12[CH2:14][O:15][C:8]([C:5]3[CH:6]=[N:7][C:2]([C:24]#[C:23][Si:20]([CH3:22])([CH3:21])[CH3:19])=[CH:3][CH:4]=3)([O:13][CH2:12]1)[O:9][CH2:10]2)[CH2:17][CH3:18]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Bis-triphenylphosphine palladium dichloride (15 mg) and cuprous iodide (5 mg) were added to a stirred solution of 1-(6-iodo-3-pyridyl)-4-n-propyl-2,6,7-trioxabicyclo[2.2.2] octane (430 mg.) and trimethylsilyl acetylene (252 μl) in dry diethylamine (10 ml) under nitrogen. The resulting mixture was stirred at room temperature for 4 hours. The solvent was removed in vacuo and the residue extracted with diethyl ether. The ethereal solution was washed with water, dried over anhydrous magnesium sulphate and evaporated in vacuo. The residue was purified by column chromatography on alumina (Alumina Woelm TSC), eluting with 1:6 dichloromethane:hexane, saturated with ammonia. 4-n-Propyl-1-[6-(2-trimethylsilylethynyl)-3-pyridyl]-2,6,7-trioxabicyclo[2.2.2]octane (282 mg) was obtained as a pale brown crystalline solid.