Methyl iodide → 4-(3-methoxymethoxy-4-methyl-phenyl)-1-methyl-1H-[1,2,3]triazol

Participants

Reaction Conditions

Reaction Steps

To a suspension of 4-ethynyl-2-methoxymethoxy-1-methyl-benzene (0.64 g, 3.63 mmol) (from Example 19 supra), iodomethane (0.23 mL, 3.63 mmol) (Aldrich) and sodium azide (0.24 g, 3.63 mmol) (Aldrich) in a mixture of water (6 mL) and t-butanol (6 mL) was added copper powder (0.17 g, 2.68 mmol) and aqueous copper sulphate solution (1 N, 0.7 mL). The reaction mixture was heated at 125° C. for 20 minutes in a microwave reactor. After cooling, the reaction mixture was partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate (2×). The combined organic phase was washed with water and brine, dried (MgSO4) and concentrated. The residue was purified by flash chromatography eluting with 5-60% ethyl acetate in hexanes to give 4-(3-methoxymethoxy-4-methyl-phenyl)-1-methyl-1H-[1,2,3]triazol. (Yield 0.57 g, 67%).

Provenance & Evidence