2-Naphthol → 5-(2-Naphthalenyloxy)-2,4-thiazolidinedione

Participants

Reaction Steps

By a procedure similar to that of method B, a solution of 2-naphthol (5.0 g, 35 mmol ) and 5-bromo-2,4-thiazolidinedione (6.8 g, 35 mmol) in THF (200 mL) was treated with lithium bis(tri-methylsilyl)amide (76 mL, 76 mmol, 1.0M in THF) to give, after chromatography (acid-washed silica gel, chloroform/acetonitrile), 5-(2-Naphthalenyloxy)-2,4-thiazolidinedione (2.8 g, 31% yield): mp 221°-222° C. (acetone/ethyl acetate); 1H NMR (DMSO-d6, 400 MHz) δ6.52 (s, 1H, OCH), 7.1-8.0 (m, 6H, ArH), 10.57 (s, 1H, ArH).

Provenance & Evidence