Diethylamine → HCID 178447864, compound

HRID 1857894Notes

Reaction equation

HRID 1857894 reaction equation
C(NCC)C.[CH2:6]([C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]#[C:22]I)=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)[CH2:7][CH3:8].[CH3:24][Si:25]([C:28]#[CH:29])([CH3:27])[CH3:26]>[Cu](I)I.O>[CH2:6]([C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]#[C:22][C:29]#[C:28][Si:25]([CH3:27])([CH3:26])[CH3:24])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)[CH2:7][CH3:8]

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 66111TrimethylsilylacetyleneHCID 178447870HCID 178447870, compound

Product 1

HCID 178447864HCID 178447864, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 962WaterSolvent

Procedure

To a mixture of dichlorobistriphenylphosphine palladium (4.2 mmol) and copper iodide (0.64 mmol) was added diethylamine, and stirred at room temperature under argon gas atmosphere for 30 minutes. Then, 4-(trans-4-propylcyclohexyl)-1-(2-iodoethynyl)benzene (0.12 mol) was added thereto, and further stirred at room temperature for 15 minutes. To this reaction mixture was added (trimethylsilyl)acetylene (0.14 mol), and stirred at room temperature overnight. After completion of the reaction, water was added thereto and extracted with toluene twice. The organic layer thus obtained was washed with water, and then dried over anhydrous magnesium sulfate. After it was subjected to filtration, the solvent was distilled off under a reduced pressure. The residue was purified by column chromatography (silica gel/heptane) and recrystallization (ethanol) to obtain colorless crystals of 4-(trans-4-propylcyclohexyl)-1-(4-trimethylsilyl-1,3-butadiyne-1-yl)benzene. (Yield 24%).

Workup

  1. stirringfurther stirred at room temperature for 15 minutes
  2. stirringstirred at room temperature overnight
  3. additionwas added
  4. extractionextracted with toluene twice
  5. customThe organic layer thus obtained
  6. washwas washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationAfter it was subjected to filtration
  9. distillationthe solvent was distilled off under a reduced pressure
  10. customThe residue was purified by column chromatography (silica gel/heptane) and recrystallization (ethanol)

Sources & evidence

ORD record
ord-e4a857a20222400b803960960cfb4566
Source dataset
uspto-grants-2000_11
Patent number
US06149838

Reaction notes

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