Triethylamine → HCID 102137475, compound

HRID 349726Notes

Reaction equation

HRID 349726 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.C(N(CC)CC)C.O1CCOCC1.[CH:22]([N:25]([BH2:29])[CH:26]([CH3:28])[CH3:27])([CH3:24])[CH3:23]>[Pd].CCOCC>[C:5]1([CH3:8])[CH:6]=[CH:7][C:2]([BH:29][N:25]([CH:26]([CH3:28])[CH3:27])[CH:22]([CH3:24])[CH3:23])=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 122074-IodotolueneHCID 312751,4-DioxaneHCID 101672200HCID 101672200, compound

Product 1

HCID 102137475HCID 102137475, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
70 °C

Procedure

0.343 g (0.49 mmol) of palladium catalyst (Ph3P)2PdCl2, 2.129 g (9.8 mmol) of p-iodotoluene, 6.8 ml (49 mmol) of triethylamine, 30 ml of dioxane and 3 ml (19.5 mmol) of diisopropylaminoborane were introduced into a 250 ml Schlenk vessel dried beforehand under argon. The Schlenk vessel was subsequently equipped with a reflux condenser connected at the top to a bubbler. The reaction mixture was stirred magnetically and heated at 70° C. for 15 h. The reaction mixture was subsequently allowed to return, under argon, to ambient temperature. The solvent and the excess reactants were evaporated under the vacuum of a vane pump. The residue obtained was taken up in anhydrous ether and then filtered under argon through dry Celite® 545. The filtrate was again evaporated and the residue was distilled in a Kügelrohr distillation apparatus (T=30–35° C.) under a vacuum of 0.01 mmHg. 1.694 g (Yd=85%) of a colorless oil were isolated. The spectroscopic characteristics are as follows:

Workup

  1. customdried
  2. customThe Schlenk vessel was subsequently equipped with a reflux condenser
  3. customto return, under argon, to ambient temperature
  4. customThe solvent and the excess reactants were evaporated under the vacuum of a vane pump
  5. customThe residue obtained
  6. filtrationfiltered under argon
  7. customthrough dry Celite® 545
  8. customThe filtrate was again evaporated
  9. distillationthe residue was distilled in a Kügelrohr distillation apparatus (T=30–35° C.) under a vacuum of 0.01 mmHg
  10. custom1.694 g (Yd=85%) of a colorless oil were isolated

Sources & evidence

ORD record
ord-dafb14074f9b43cba8ffb24a4a15f7e9
Source dataset
uspto-grants-2007_02
Patent number
US07179940B2

Reaction notes

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