Iodine → HCID 13259985, compound

Participants

Reaction Conditions

Reaction Steps

1.58 g (0.058 mol) of aluminum (in the form of flakes) are covered with 7.3 ml of tetrahydrofuran, and a catalytic amount (0.05 g) of mercury(II) chloride and one iodine crystal are added. After standing at 20° C. for 12 hours, 10.3 g (0.087 mol) of propargyl bromide in 11 ml of tetrahydrofuran are added dropwise at 60° C. The mixture is then cooled down to -60° C. and a solution of 17.1 g (0.05 mol) of 5-(2,4-dichlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-pentanone in 20 ml of tetrahydrofuran is added dropwise. The temperature is allowed to rise to 0° C., this temperature is maintained for a further hour and 22 ml of a saturated aqueous solution of ammonium chloride are added. The mixture is then filtered, the filtrate is evaporated in vacuo and the residue is taken up in 200 ml of ethyl acetate. After washing three times with 100 ml of water each time, the organic phase is dried over sodium sulphate and then evaporated in vacuo. Solvent residues are removed at 50° C. and 0.01 mbar. 14.3 g (74.8% of theory) of 7-(2,4-dichlorophenoxy)-5,5-dimethyl-4-(1,2,4-triazol-1-ylmethyl)-1-heptin-4-ol are obtained as a brownish oil of refractive index nD20 =1.5642.

Provenance & Evidence