Reaction #93301

Reaction equation

bromochloromethane

ether

2-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)-1,2-propanediol

sodium hydride

→

4-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-4-(1H-1,2,4-triazol-1-yl)methyl-1,3-dioxolane

Yield 54.4%

Solvents

dimethylformamide

Conditions

Workup

1. 1
   Otherto react at a temperature of 50° C. for 1 hour
2. 2
   WashThe ethereal layer is washed with water
3. 3
   Dryingdried over anhydrous sodium sulfate
4. 4
   Concentrationconcentrated
5. 5
   OtherThe residue is chromatographed on a column of silica-gel, which
6. 6
   Washis eluted with 3% methanol-methylene chloride
7. 7
   ConcentrationThe eluate is concentrated
8. 8
   Otherthe residue is crystallized from ethyl acetate

Procedure

To a solution of 500 mg of 2-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)-1,2-propanediol in 5 ml of dry dimethylformamide is added 180 mg of 50% mineral oil dispersion of sodium hydride under ice cooling. Five minutes later 490 mg of bromochloromethane is added to the mixture, which is allowed to react at a temperature of 50° C. for 1 hour. The reaction mixture is mixed with ice water and shaken with ether. The ethereal layer is washed with water, dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed on a column of silica-gel, which is eluted with 3% methanol-methylene chloride. The eluate is concentrated and the residue is crystallized from ethyl acetate to give 280 mg of 4-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-4-(1H-1,2,4-triazol-1-yl)methyl-1,3-dioxolane as crystals melting at 201 ° to 203° C. The yield is 54%.

Source