TMS-Imidazole → HCID 54455995, compound

HRID 2198899Notes

Reaction equation

HRID 2198899 reaction equation
Cl[CH:2]=[C:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:4](=[O:9])[C:5]([CH3:8])([CH3:7])[CH3:6].C[Si]([C:22]1[NH:23][CH:24]=[CH:25][N:26]=1)(C)C>C1(C)C=CC=CC=1>[N:23]1([CH:2]=[C:3]([O:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[C:4](=[O:9])[C:5]([CH3:8])([CH3:7])[CH3:6])[CH:24]=[CH:25][N:26]=[CH:22]1

Participants

4

Reactant 2

HCID 14420972TMS-ImidazoleHCID 53969116HCID 53969116, compound

Product 1

HCID 54455995HCID 54455995, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

13 g (0.05 mols) of 1-chloro-2-(4-chlorophenoxy)-4,4-dimethyl-1-penten-3-one and 7 g (0.05 mole) of trimethylsilylimidazole in 50 ml of toluene were heated under reflux for 5 hours. Thereafter, the reaction mixture was concentrated by distilling off the solvent in vacuo and the oily residue was separated by column chromatography (silica gel; ethyl acetate: chloroform=1:2). 9 g (58% of theory) of 1-(imidazol-1-yl)-2-(4-chlorophenoxy)-4,4-dimethyl-1-penten-3-one of melting point 94°-95° C. were obtained. ##STR54##

Workup

  1. temperatureunder reflux for 5 hours
  2. concentrationThereafter, the reaction mixture was concentrated
  3. distillationby distilling off the solvent in vacuo
  4. customthe oily residue was separated by column chromatography (silica gel; ethyl acetate: chloroform=1:2)

Sources & evidence

ORD record
ord-03925dcd11ab453c8e4a133fb2b011e9
Source dataset
uspto-grants-1982_11
Patent number
US04360528

Reaction notes

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