Trimethylsilylacetylene → HCID 19992007, compound

HRID 345292Notes

Reaction equation

HRID 345292 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

HCID 66111TrimethylsilylacetyleneHCID 3086954Pyridine, 2-iodo-5-(4-propyl-2,6,7-trioxabicyclo(2.2.2)oct-1-yl)-

Product 1

HCID 19992007HCID 19992007, compound

Reagents, catalysts & solvents 1

HCID 8021DiethylamineSolvent

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.

Workup

  1. customThe solvent was removed in vacuo
  2. extractionthe residue extracted with diethyl ether
  3. washThe ethereal solution was washed with water
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on alumina (Alumina Woelm TSC)
  7. washeluting with 1:6 dichloromethane

Sources & evidence

ORD record
ord-3a552aeff9ab4b4d90bae93b318d452d
Source dataset
uspto-grants-1991_10
Patent number
US05057504

Reaction notes

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