Trimethylsilylacetylene → HCID 15021947, compound

HRID 1089136Notes

Reaction equation

HRID 1089136 reaction equation
[CH2:1]([C:3]12[CH2:10][O:9][C:6]([C:11]3[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=3)([O:7][CH2:8]1)[O:5][CH2:4]2)[CH3:2].[CH3:18][Si:19]([C:22]#[CH:23])([CH3:21])[CH3:20]>C(NCC)C>[CH2:1]([C:3]12[CH2:10][O:9][C:6]([C:11]3[CH:16]=[CH:15][C:14]([C:23]#[C:22][Si:19]([CH3:21])([CH3:20])[CH3:18])=[CH:13][CH:12]=3)([O:7][CH2:8]1)[O:5][CH2:4]2)[CH3:2]

Participants

4

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 150219464-Ethyl-1-(4-iodophenyl)-2,6,7-trioxabicyclo[2,2,2]octane

Product 1

HCID 15021947HCID 15021947, compound

Reagents, catalysts & solvents 1

HCID 8021DiethylamineSolvent

Procedure

Bis-triphenylphosphine palladium dichloride (60 mg) and cuprous iodide (10 mg) were added to a stirred solution of 4-ethyl-1-(4-iodophenyl)-2,6,7-trioxabicyclo[2,2,2]octane (1.5 gms) and trimethylsilylacetylene (0.92 ml) in dry diethylamine (40 ml) under nitrogen. The resulting mixture was stirred at room temperature for 16 hours. After this time the solvent was removed under vacuum and the residue extracted with diethylether. 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, eluting with 30% dichloromethane in hexane saturated with ammonia. 4-Ethyl-1-[4-(2-trimethylsilylethynyl)-phenyl]-2,6,7-trioxabicyclo[2,2,2]octane (1.2 gms) was obtained as an off-white solid (1.2 gms) after recrystallisation from hexane.

Workup

  1. customAfter this time the solvent was removed under vacuum
  2. extractionthe residue extracted with diethylether
  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
  7. washeluting with 30% dichloromethane in hexane saturated with ammonia

Sources & evidence

ORD record
ord-8bd203fabcca47c9bdb33f3a63246fee
Source dataset
uspto-grants-1990_10
Patent number
US04965257

Reaction notes

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