Pyridine → HCID 86740731, compound

Participants

Reaction Steps

A mixture of 5-{4-[2-(5-ethyl-2-pyridyl)-3-hydroxypropoxy]benzyl}-2,4-thiazolidinedione sodium salt (408 mg), pyridine (10 ml) and acetic anhydride (0.15 ml) was stirred at room temperature for 8 hours, and poured in water, followed by extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and freed of the solvent. The residue was chromatographed on a silica-gel (20 g) column and elution was effected with benzene-acetone (10:1, V/V) to give 5-{4-[3-acetoxy-2-(5-ethyl-2-pyridyl)propoxy]benzyl}-2,4-thiazolidinedione in the form of an oily substance. Yield of 350 mg (81.8%). IR(Neat): 1740, 1690, 1230 cm-1. NMR (CDCl3)δ: 1.24(3H,t,J=7 Hz), 2.00(3H,s), 2.64(2H,q,J=7 Hz), 3.03(1H,dd,J=14 and 9 Hz), 3.45(1H,dd,J=14 and 9 Hz), 3.60 (1H,m), 4.31(2H,d,J=5 Hz), 4.47(1H,dd,J=9 and 4 Hz), 4.55 (2H,d,J=5 Hz), 6.80(2H,d,J=9 Hz), 7.10(2H,d,J=9 Hz), 7.20(1H,d, J=8 Hz), 7.48(1H,dd,J=8 and 2 Hz), 8.42(1H,d,J=2 Hz).

Provenance & Evidence