Formaldehyde → (Z)-5-(4-ethoxybenzylidene)-3-(2-(methylamino)ethyl)thiazolidine-2,4-dione

Participants

Reaction Steps

To a solution of compound 76 (122 mg, 0.30 mmol) in 4 mL of 1,2-dichloroethane was added triethylamine (84 μL, 0.60 mmol), aqueous formaldehyde (37%, 24 μL, 0.30 mmol) and sodium triacetoxyborohydride (254 mg, 1.20 mmol). The reaction mixture was allowed to stir overnight at room temperature. The reaction was quenched by adding sat'd aqueous NaHCO3 and stirred at room temperature for 20 min. The reaction mixture was partitioned between ethyl acetate and sat'd aqueous NaHCO3, the organic layer was washed with brine, collected, dried over anhydrous Na2SO4, filtered, concentrated and purified by silica column chromatography using dichloromethane/methanol/NH4OH (ratio: 92/7/1) to afford compound 23a (38.1%, 35 mg) as a yellow solid.

Provenance & Evidence