Tetrahydrofuran → HCID 89544083, compound

HRID 1750755Notes

Reaction equation

HRID 1750755 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].C([N:12]([CH2:15][CH3:16])CC)C.[CH2:17]1[CH2:21]O[CH2:19][CH2:18]1>>[CH:5]([C:4]1[CH:3]=[C:2]([C:19]#[C:18][C:17]2[CH:21]=[C:3]([C:4]#[C:16][C:15]#[N:12])[CH:2]=[CH:9][CH:8]=2)[CH:9]=[CH:8][CH:7]=1)=[O:6]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 2526103-Iodobenzaldehyde

Product 1

HCID 89544083HCID 89544083, compoundYield 55%

Procedure

87 mg of (3-ethynyl-phenyl)-1-propyne nitrile 63 (0.576 mmol), 120.3 mg of 3-iodobenzaldehyde, and 0.8 ml triethylamine (58.5 mg, 0.576 mmol) were dissolved in 1.5 ml of anhydrous THF, and the solution was deoxygenated by purging argon in it. To this solution was added 22 mg of tetrakistriphenylphosphine palladium (0.019 mmol) then the reaction was allowed to stir for 20 min at room temperature. To this stirring mixture was added 0.9 mg of cuprous iodide (4.5×10−3) then stirred at room temperature for 2 hr, followed by heating further at 50° C. for 2 hr. The solvent was then evaporated in rotatory evaporation to give brown solid. The residue was then purified by silica gel column chromatography using 1:9 dichloromethane:hexane to collect starting material. The polarity was increased to 2:8 dichloromethane:hexane to afford 80 mg of 61 as a golden solid in 55% yield. 1H NMR δ 10.2 (s, 1H), 8.04 (sm, 1H), 7.89 (dm, 1H, J=7.7), 7.78 (m, 2H), 7.69 (dm, 1H, 7.8), 7.60 (dm, 1H, J=7.8), 7.56 (t, 1H, J=7.7), 7.44 (t, 1H, J=7.8); 13C NMR δ 191.30, 137.13, 136.59, 136.27, 134.81, 133.21, 132.90, 129.61, 129.26, 123.99, 123.69, 118.16, 105.22, 89.72, 88.64, 81.77, 63.62; LRMS (GC/MS, CH2Cl2) m/e 255 (M+)

Workup

  1. customthe solution was deoxygenated
  2. customby purging argon in it
  3. stirringthen stirred at room temperature for 2 hr
  4. temperatureby heating further at 50° C. for 2 hr
  5. customThe solvent was then evaporated in rotatory evaporation
  6. customto give brown solid
  7. customThe residue was then purified by silica gel column chromatography
  8. customhexane to collect
  9. temperatureThe polarity was increased to 2:8 dichloromethane

Sources & evidence

ORD record
ord-01e6bfe09ab24777be954f9d108a401a
Source dataset
uspto-grants-2015_10
Patent number
US09156862B2

Reaction notes

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