tert-Butanol → HCID 59363634, compound

Participants

Reaction Steps

To a solution of 6-Methyl-pyridine-2,3-dicarboxylic acid 2-methyl ester (CAS:[135338-27-1]) (4.93 g, 25 mmol) and N-methylmorpholine (3.05 ml, 2.81 g, 28 mmol, 1.1 equiv.) in methylene chloride (100.0 ml) was added diphenylphosphoryl-azide (DPPA, 6.14 ml, 7.88 g, 28 mmol, 1.1 equiv.) dropwise at room temperature. The mixture was stirred for 30 min at r.t. and then heated to 70° C. for 2 h whereby nitrogen evolution is observed. Then tert-Butanol (3.56 ml, 2.81 g, 38 mmol, 1.5 equiv.) and copper(I) chloride (25 mg, 0.25 mmol, 0.01 equiv.) were added and the mixture was heated at 70° C. for another 4 h. The reaction mixture was allowed to cool to r.t., stirred overnight, and concentrated in vaccuo. The resulting dark brown oil (16.9 g) was purified by flash chromatography (heptane/ethyl acetate 3:2) to yield the title compound as a white solid (total 5.06 g, 75%), MS (ISP): m/e=267.2 (M+H+).

Provenance & Evidence