Toluene → HCID 73445650, compound

Participants

Reaction Steps

A mixture of toluene (35 mL), piperidine (145 μL), acetic acid (145 μL), 3-(5-isobutyl-3,3-dimethyl-2,3-dihydro-benzofuran-7-yl)-4-trifluoromethoxy-benzaldehyde (5.7 g, 14.53 mmol) and 2,4-thiazolidinedione (1.7 g, 14.53 mmol) was heated at reflux for 20 hrs. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, washed with water and brine, dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica gel (0 to 20% ethylacetate in hexane) and further recrystallised from ethanol/water to afford 5.15 g (72%) of 5-[3-(5-Isobutyl-3,3-dimethyl-2,3-dihydro-benzofuran-7-yl)-4-trifluoromethoxy-benzylidene]-thiazolidine-2,4-dione. mp 142–146° C. 1H-NMR (300 MHz, DMSO-d-6): 0.87 (d, J=6.9 Hz, 6H), 1.31 (s, 6H), 1.81 (m, 1H), 2.44 (d, J=6.9 Hz, 2H), 4.19 (s, 2H), 6.91 (d, J=1.5 Hz, 1H), 7.07 (d, J=1.5 Hz, 1H), 7.58 (d, J=8.4 Hz, 1H), 7.70 (dd, J1=8.4 Hz, J2=2.4 Hz, 1H), 7.75 (d, J=2.1 Hz, 1H), 7.86 (s, 1H), 12.70 (br s, 1. The intermediate 3-(5-isobutyl-3,3-dimethyl-2,3-dihydro-benzofuran-7-yl)-4-trifluoromethoxy-benzaldehyde was prepared as follows:

Provenance & Evidence