Hydrochloric Acid → HCID 11136557, compound

HRID 1522724Notes

Reaction equation

HRID 1522724 reaction equation
I[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:21][Si:22]([C:25]#[CH:26])([CH3:24])[CH3:23].Cl>[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.ClCCl.O>[CH3:21][Si:22]([C:25]#[C:26][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1)([CH3:24])[CH3:23]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 11967290HCID 11967290, compound

Product 1

HCID 11136557HCID 11136557, compoundYield 96%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of (15) (128 mg, 0.46 mmol), copper(I) iodide (9 mg, 50 μmol) and triethylamine (10 cm3) was deoxygenated with argon. Tetrakis(triphenylphosphine)palladium(0) (26 mg, 23 μmol) was added, and the mixture was deoxygenated with argon again. Trimethylsilylacetylene (0.15 cm3, 1 mmol) was added, and the reaction was stirred at room temperature for 9 hours. Water (50 cm3), aqueous hydrochloric acid (3 M, 5 cm3) and dichloromethane (50 cm3) were added, and the layers were separated. The organic layer was washed with brine (50 cm3) and dried over magnesium sulfate, and the solvent was removed to leave a black solid. The crude product was purified by column chromatography using dichloromethane: light petroleum 3:2 as eluent, to give (16) as a pale brown oil (110 mg, 96%).

Workup

  1. customwas deoxygenated with argon
  2. customthe mixture was deoxygenated with argon again
  3. customthe layers were separated
  4. washThe organic layer was washed with brine (50 cm3)
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was removed
  7. customto leave a black solid
  8. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-b5fa6f4032bd49158cff2b86b298dffe
Source dataset
uspto-grants-2015_07
Patent number
US09078330B2

Reaction notes

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