Isopropanol → HCID 57238292, compound

Participants

Reaction Steps

To a solution of 5-[2-hydroxy-1-(1-naphthalenyl)ethylidene]-2,4-thiazolidinedione (10.13 g, 35.5 mmol) in acetone (250 mL) at 0° C. was added Jones reagent (8N, 10.26 mL, 82 mmol). After 30 min 2-propanol (10 mL) was added. The reaction mixture was filtered and concentrated in vacuo. The resulting oil was taken up in ether and washed with water (2×). The organic phase was dried over magnesium sulfate, filtered and concentrated to give a foam (9.88 g). Recrystallization (chloroform/ethyl acetate) gave crystals (6.87 g) of the E-isomer. m.p. 184°-185° C.

Provenance & Evidence