Methyl 4-iodobenzoate → HCID 53671738, compound

HRID 482503Notes

Reaction equation

HRID 482503 reaction equation
[CH2:1]([O:7][C:8]1[CH:13]=[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:11]([C:21]23[CH2:30][CH:25]4[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]4)[CH2:22]2)[CH2:28]3)=[CH:10][C:9]=1[C:31]#[CH:32])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].I[C:34]1[CH:43]=[CH:42][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:36][CH:35]=1>[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(N(CC)CC)C>[CH2:1]([O:7][C:8]1[CH:13]=[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:11]([C:21]23[CH2:22][CH:23]4[CH2:29][CH:27]([CH2:26][CH:25]([CH2:24]4)[CH2:30]2)[CH2:28]3)=[CH:10][C:9]=1[C:31]#[C:32][C:34]1[CH:43]=[CH:42][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:36][CH:35]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 2

HCID 69273Methyl 4-iodobenzoateHCID 23205506HCID 23205506, compound

Product 1

HCID 53671738HCID 53671738, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

1.8 g (4.1 mmol) of 2,4-dihexyloxy-5-(1-adamantyl)phenylacetylene, 1.2 g (4.5 mmol) of methyl 4-iodobenzoate and 15 ml of triethylamine were introduced into a three-necked flask. The reaction mixture was degassed with nitrogen for 15 min, 100 mg of copper iodide and 260 mg (0.37 mmol) of bis(triphenylphosphine)-palladium(II) chloride were added and stirring was carried out at room temperature for twelve hours. The reaction mixture was evaporated to dryness, the residue was taken up in water and ethyl ether and the organic phase was separated by settling, dried over magnesium sulfate and evaporated.

Workup

  1. customThe reaction mixture was degassed with nitrogen for 15 min
  2. waitwas carried out at room temperature for twelve hours
  3. customThe reaction mixture was evaporated to dryness
  4. customethyl ether and the organic phase was separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-0ed3bbbbfaef4609aebf79cb86898e26
Source dataset
uspto-grants-1998_08
Patent number
US05798354

Reaction notes

Loading…