Reaction #1687627

Reaction equation

ethyl acetate

diazomethane

68

4-(3-Pyridyl)-1,2,3-triazole

acetic acid

→

2-Methyl-4-(3-pyridyl)-1,2,3,-triazole

Solvents

ether

ethanol

Conditions

Workup

1. 1
   Otherthe mixture was evaporated in vacuo
2. 2
   workup.ADDITIONWater (75 ml) was added
3. 3
   ExtractionExtraction with 3×100 ml of ether
4. 4
   Dryingdrying of the organic phase over magnesium sulphate, and removal of the solvent in vacuo
5. 5
   Othergave a brown solid which
6. 6
   Othergiving a colorless solid, 69

Procedure

A solution of ca. 3.0 g (0.070 mol) diazomethane in ether was added dropwise to a solution of 6.0 g (0.04 mol) of 68 in 150 ml of ethanol at room temperature. The solution was stirred overnight at ambient temperature. Ca. 1 ml of acetic acid was added and the mixture was evaporated in vacuo. Water (75 ml) was added and the solution made basic with ammonia. Extraction with 3×100 ml of ether, drying of the organic phase over magnesium sulphate, and removal of the solvent in vacuo gave a brown solid which as applied to a silica gel column (eluent: ethyl acetate) giving a colorless solid, 69. Yield: 2.8 g (0.018 mol, 43%).

Source