tert-Butanol → HCID 18966278, compound

Participants

Reaction Steps

In a flask were placed 10 g (0.047 mole) of 2,2-dimethyl-5-fluoro-1,3-benzodioxol-4-ylcarboxylic acid, 12.98 g (0.0471 mole) of diphenylphosphoryl azide, 4.77 g (0.0471 mole) of triethylamine, and 80 mL of t-butanol. This mixture was heated at reflux for approximately 16 hours, after which the solvent was evaporated under reduced pressure. The residue was passed through a column of silica gel, eluting first with a ;methylene chloride/heptane mixture and finally with pure methylene chloride. The product-containing fractions were combined, and the solvents were evaporated under reduced pressure, leaving 11.9 g of t-butyl N-(2,2-dimethyl-5-fluoro-1,3-benzodioxol-4-yl)carbamate as a residue, mp 106-107° C. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence