Triethylamine → HCID 54019290, compound

HRID 638619Notes

Reaction equation

HRID 638619 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11](I)[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[CH2:40]([N:43]1[CH:47]=[CH:46][N:45]=[CH:44]1)[CH:41]=[CH2:42]>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:12]=[C:11]([CH:42]=[CH:41][CH2:40][N:43]2[CH:47]=[CH:46][N:45]=[CH:44]2)[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 357941-Allyl-1H-imidazoleHCID 13287888Ethyl 2-chloro-4-iodobenzoate

Product 1

HCID 54019290HCID 54019290, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of ethyl 2-chloro-4-iodobenzoate (0.92 g, 2.96 mmol), triphenylphosphine (0.014 g, 0.0534 mmol), triethylamine (0.58 g, 5.73 mmol), 1-allylimidazole (1.2 g, 11.1 mmol), and palladium acetate (0.007 g) in acetonitrile (0.6 ml) was stirred and heated at 120° for 6 h in a steel bomb. The reaction mixture was cooled and concentrated to give an oily solid. The solid was purified by `flash` chromatography to give 1-[3-(3-chloro-4-ethoxycarbonylphenyl)prop-2-enyl]imidazole as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. customto give an oily solid
  4. customThe solid was purified by `flash` chromatography

Sources & evidence

ORD record
ord-9ee3fbaefbde40c9bb08eb92a217107d
Source dataset
uspto-grants-1985_12
Patent number
US04562199

Reaction notes

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