1,2-Dichloroethane → HCID 11761020, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-8 (1.49 g, 3.96 mmol) in ethanol (8 mL) was added NaOH (4.36 mL 1M solution in water, 4.36 mmol). After stirring for 1 h at 50° C., HCl (4.75 mL of a 1M solution in water, 4.75 mmol) was added, 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 chloroform (15 mL), and triethylamine (2.75 mL, 19.8 mmol), N,O-dimethylhydroxylamine hydrochloride (0.772 g, 7.92 mmol), HOBT (1 g) and EDC (0.91 g, 4.75 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 gave 2-9 as a yellow oil. TLC Rf =0.49 (silica, 70:25:5 chloroform /ethyl acetate /methanol) 1H NMR (300 MHz, CDCl3) δ 7.05 (m, 1H), 6.38 (m, 1H), 4.81 (br s, 1H), 3.69, m, 3H), 3.37 (m, 4H), 3.18 (s, 3H), 2.64 (m, 2H), 2.53 (m, 2H), 1.88 (m, 4H), 1.44 (m, 9H).

Provenance & Evidence