Boron Trichloride → HCID 10383657, compound

Participants

Reaction Steps

A solution of 2.15 (0.036 g, 0.08 mmol) in CH2Cl2 (4 mL) was cooled to -78° C., treated with boron trichloride (1.0M in dichloromethane, 0.24 mL, 0.24 mmol), and stirred at that temperature for 1.5 h. The reaction mixture was quenched by the slow addition of a saturated NaHCO3 solution (0.3 mL) at -78° C., and immediately partitioned between ice-cold ether and a pH 7 buffer solution. The organic layer was washed five times with the pH 7 buffer solution, dried (Na2SO4), and concentrated to give a white solid. This solid was washed with cold hexane several times to give a pure sample of 2.2 (24 mg, 84%) as a solid; mp 65°-66° C.; [α]22D +1.43° (c 4.2, CHCl3). The IR, 1H NMR, and 13C NMR were identical to those reported for the racemate (3e, Example 1).

Provenance & Evidence