Carbon Tetrachloride → HCID 14308627, compound

Participants

Reaction Steps

895 mg (3.08 mmol) of 1,5-anhydro-2,3,4-tri-O-acetyl-D-glucitol was dissolved in 30 ml of pyridine, and 1.95 g (7.4 mmol) of triphenylphosphine and 10 ml of carbon tetrachloride were added. The mixture was allowed to react at 45° to 50° C. for 2 hours. The reaction mixture was then concentrated under reduced pressure and the residue extracted with chloroform (80 ml). The chloroform layer was washed with 1N aqueous hydrochloric acid solution (80 ml) and water (80 ml), dehydrated over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to column chromatography (Waggle C-200, 40 g) and eluted with chloroform-methanol (300:1). The eluate was crystallized from ethyl acetate-hexane to obtain 562 mg (1.82 mmol, 59%) of 1,5-anhydro-6-chloro-6-deoxy-2,3,4-tri-O-acetyl-D-glucitol as a colorless needle crystal. Shown below are physicochemical properties of the crystalline compound thus obtained.

Provenance & Evidence