Triethylamine → HCID 58805509, compound

HRID 349727Notes

Reaction equation

HRID 349727 reaction equation
I[C:2]1[CH:7]=CC(C)=[CH:4][CH:3]=1.C(N(CC)CC)C.O1[CH2:21][CH2:20][O:19][CH2:18]C1.[CH:22]1([N:28]([BH2:35])[CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>[Pd].CCOCC>[CH3:18][O:19][C:20]1[CH:21]=[CH:4][C:3]([BH:35][N:28]([CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)=[CH:2][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 122074-IodotolueneHCID 312751,4-DioxaneHCID 101758441HCID 101758441, compound

Product 1

HCID 58805509HCID 58805509, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
70 °C

Procedure

1.130 g (0.19 mmol) of palladium catalyst (Ph3P)2PdCl2, 0.868 g (3.7 mmol) of p-iodotoluene, 2.5 ml (18.5 mmol) of triethylamine, 15 ml of dioxane and 0.708 g (3.7 mmol) of dicyclohexylaminoborane were introduced into a 100 ml Schlenk vessel dried beforehand under argon. The Schlenk vessel was subsequently equipped with a reflux condenser connected via 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=40° C.) under a vacuum of 0.01 mmHg. 0.884 g (Yd=81%) of a white solid was 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=40° C.) under a vacuum of 0.01 mmHg
  10. custom0.884 g (Yd=81%) of a white solid was isolated

Sources & evidence

ORD record
ord-787190f847004fcb9b2c2eca9f3b86b0
Source dataset
uspto-grants-2007_02
Patent number
US07179940B2

Reaction notes

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