18-Crown-6

The Uses of 18-Crown-6

18-Crown-6 is used as an efficient phase transfer catalyst and as a complexing agent with a variety of small cation. It is involved in the synthesis of diaryl ethers, diaryl thioethers, and diarylamines mediated by potassium fluoride-alumina and 18-crown-6. It facilitates the solubility of potassium permanganate in benzene, which is used for oxidizing the organic compounds. It is used to accelerate various substitution reactions as well as enhances the power of nucleophiles such as potassium acetate. It is utilized in the alkylation reactions in the presence of potassium carbonate, N-alkylation of glutarimide and succinimide with dimethylcarbonate. The complex formed by its reaction with potassium cyanide acts as a catalyst in the cyanosilylation of aldehydes, ketones and quinines with trimethylsilyl cyanide (TMSCN).

The Uses of 18-Crown-6

To a solution of the SM (1 g, 2 mmol) in anhydrous THF (20 mL) at 0 C was added NaH (288 mg, 12 mmol). The mixture was stirred at 0 C for 30 min. Iodomethane (1.65 g, 12 mmol) was added and the reaction mixture was stirred at RT for 12 h. The mixture was quenched with H2O, dried, and concentrated. The crude residue was purified by silica gel chromatography (10-50% EtOAc/hexane) to provide the product as a yellow solid. [475 mg, 46%]