Ammonium Chloride → HCID 20456205, compound

Participants

Reaction Conditions

Reaction Steps

0.1 g of sodium was dissolved in 10 ml of methanol, under nitrogen. 1.5 g of 3A was stirred in 12 ml of dry methanol at 0° C. under nitrogen and 0.23 ml of the sodium methoxide solution was added drop-by-drop at 0° C. The resulting mixture was stirred at 0° C. for 3.5 hours, then stored in a freezer over a week-end. Then 30 mg of ammonium chloride was added, the mixture was stirred for 15 minutes at 0° C., stripped to a mush, slurried with ether and filtered. The ether was evaporated from the filtrate, the residue was dissolved in 25 ml of tetrahydrofuran and the solution was added drop-by-drop over one minute to a vigorously stirred ice-cold 0.2N hydrochloric acid solution. The resulting mixture was stirred at 0° C. for 3.5 hours, the solvent was evaporated and the residue was extracted with ether. The water was evaporated from the aqueous phase, toluene was added to the residue and residual water removed by azeotropic distillation. The residue was dissolved in methanol, toluene was added and the mixture was distilled azeotropically. The residue was dissolved in methylene chloride, the solution was dried (Na2SO4), filtered and the solvent was evaporated. The residue was subjected to low pressure distillation, to give 3, as a gum.

Provenance & Evidence