Piperidine → 5-(4-beta-D-Galactopyranosyloxy-3-methoxyphenylmethylene)-3-(4-hydroxyphenyl)-2-thioxothiazolidin-4-one

Participants

Reaction Steps

3-(4-Hydroxyphenyl)-2-thioxothiazolidin-4-one (0.23 g, 1.0 mmol) was added to a suspension of 4-formyl-2-methoxyphenyl β-D-galactopyranoside (1c)(0.32 g, 1.0 mmol) in methanol (20 ml) containing a drop of piperidine. The mixture, which rapidly turned yellow, was gently heated under reflux and deposited a thick precipitate after 30 min. The mixture was then cooled and filtered to give the required product (5c){0.12 g, 23%, m.p. decomp.>230° C., [α]D -34.4° (c 0.6, DMOS)}(Found: C, 53.04; H, 4.55; N, 2.81. C23H23NO9S2 requires C, 52.96; H, 4.44; N, 2.68%).

Provenance & Evidence