Ammonium Chloride → HCID 14747543, compound

Participants

Reaction Conditions

Reaction Steps

1(4'-Chlorophenyl)ethyne (1.43g:0.01 mole) was dissolved in tetrahydrofuran (10 ml) under nitrogen and cooled to -35° C. Butyllithium was added (6.5 ml of 1.6M solution:0.0104 mole) causing the colour to change. The mixture was stirred for 1/2 hour during which time it thickened and the colour changed to pink (from purple). Addition of a solution of chlorotanium triisopropoxide (10.6 ml or a 1 molar solution:0.0106 mole) caused the colour to change to yellow and the mixture was stirred for 20 minutes. The mixture was cooled to -60° C. and a solution of 2-methyl 1(pyrimidin-5-yl)propan-1-one in tetrahydrofuran (10 ml) was added and the reaction mixture allowed to warm up to room temperature within the cold bath. A solution of ammonium chloride in water (20%) was added and the mixture filtered. The aqueous was extracted with ethyl acetate (×3), washed (with water then brine), dried and the solvent removed in vacuo. The product was passed through silica (in ether) and then titurated with pentane and ether (0.467g: off white solid).

Provenance & Evidence