1,2-Dichloroethane → HCID 54034496, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 20-6 (23.4 g, 58.4 mmol) in ethanol (200 mL) was added NaOH (100 mL 1M solution in water, 100 mmol). After stirring for 1 h at 50° C., HCl (10.3 mL 12 M, 4.75 mmol) was added in 50 mL EtOH, and the mixture evaporated to give an oily residue. The residue was evaporated from ethanol three times, and then from acetonitrile three times, producing a yellow crusty solid which was dried under a vacuum of <2 mm Hg for 2 h. This residue was then slurried in acetonitrile (180 mL) and chloroform (180 mL), and NMM (41.7 mL, 379 mmol), N,O-dimethylhydroxylamine hydrochloride (11.9 g, 122 mmol), HOBT (10.2 g, 75.9 mmol), and EDC (14.5 g, 75.9 mmol) were added. After stirring for 15 h, the mixture was evaporated to dryness, the residue slurried in EtOAc, washed with sat. NaHCO3, brine, and dried over Na2SO4. Evaporative removal of the solvent followed by evaporation from toluene to remove the residual NMM gave 20-7 as a yellow oil.

Provenance & Evidence