Trichloroethanol → HCID 19819812, compound

Participants

Reaction Conditions

Reaction Steps

The acid from step (a) (25 g, 0.102 mol) was dissolved in THF(390 mL) and triethylamine (14.1 mL) was added. Diphenylphosphoryl azide (23.4 mL) was added and the mixture was heated at 65° C. for 5 hours. The reaction was cooled to room temperature and 2,2,2-trichloroethanol (46.1 mL) was added portionwise and then the reaction was heated to reflux for 40 hours. The reaction was cooled to 0° C. and water (40 mL), glacial acetic acid (360 mL) and zinc dust (132 g) were added. The ice bath was removed and the reaction was stirred overnight. After filtration of the reaction mixture through a bed of celite the filtrate was concentrated and the residue was dissolved in ethyl acetate (800 mL). The ethyl acetate was washed with 1N.NaOH (800 mL) and water (800 ml). The ethyl acetate layer was separated, dried (MgSO4) and concentrated to dryness. The residual oil was converted to the hydrochloride salt with ethanolic hydrogen chloride and precipitated by the addition of diethyl ether. A 1 g portion of the hydrochloride was recrystallized from ethyl acetate(20 mL)/MeOH(5 mL)/hexanes(15 mL) to give the title compound (0.8 g), mp 205°-206° C.

Provenance & Evidence