Thionyl Chloride → HCID 86738944, compound

Participants

Reaction Steps

A solution of 1 g (3.7 mmol) of methyl 2,3,6-trideoxy-4-C-methyl-3-trifluoroacetamido-α-L-lyxo-hexopyranoside (VII) in 90 ml of anhydrous benzene was treated with 2.75 ml of freshly distilled thionyl chloride and heated under reflux for 2 hours. The reaction mixture, after being cooled to room temperature, was washed with water and then treated under stirring with an aqueous solution of sodium hydrogen carbonate. The organic phase was separated off, washed with water and evaporated under vacuum to dryness to give compound (VIII), 0.82 g, 87% as a white solid; m.p. 160°-162° C., [α]D20° -180° (c=1, CHCl3). The PMR spectrum (CDCl3) showed absorptions at 1.35 (d, CH3 --C--5), 3.37 (s, CH3O), 4.37 (q, H--C--5), 4.83 (broad s, CH2 =C--4) and 4.95 δ (broad s, C--1--H).

Provenance & Evidence