Triethylamine → HCID 86702077, compound

HRID 873590Notes

Reaction equation

HRID 873590 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:13]([CH:15]1[CH2:17][CH2:16]1)#[CH:14].C(N(CC)CC)C>O1CCCC1.[Cu](I)I>[CH:15]1([C:13]#[C:14][C:8]([C:7]2[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[O:9])[CH2:17][CH2:16]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 138823Cyclopropylacetylene

Product 1

HCID 86702077HCID 86702077, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A 250-mL round bottom flask was charged with bis(triphenylphosphine)palladium bischloride (151 mg, 0.216 mmol) and copper iodide (82 mg, 0.431 mmol), and the flask was degassed with nitrogen. Tetrahydrofuran (40 mL) was added through a septum, and nitrogen was bubbled through the mixture for 30 minutes. To this was added dropwise a nitrogen-degassed solution of 4-nitrobenzoyl chloride (2g, 10 8 mmol), ethynylcyclopropane (784 mg, 11.9 mmol) and triethylamine (1.31 g, 12.9 mmol) in tetrahydrofuran (15 mL). The reaction mixture was stirred at room temperature for 2 hours and then concentrated to dryness. The residue was purified by normal phase chromatography to give the title compound.

Workup

  1. customthe flask was degassed with nitrogen
  2. additionTetrahydrofuran (40 mL) was added through a septum, and nitrogen
  3. customwas bubbled through the mixture for 30 minutes
  4. additionTo this was added dropwise a nitrogen-
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by normal phase chromatography

Sources & evidence

ORD record
ord-bac5f236b1e34197afd977eaa056c087
Source dataset
uspto-grants-2015_03
Patent number
US08975398B2

Reaction notes

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