Hydrochloric Acid → HCID 68229261, compound

Participants

Reaction Steps

To an ethanol (10 mL) suspension of (E)-2-methyl-4-((5-phenylfuran-2-yl)methylene)oxazol-5(4H)-one 47 (253 mg, 1.0 mmol) was added 12M HCl (5 mL). The reaction mixture was refluxed for 5 h, then the excess solvent was removed in vacuo. The residue was diluted with ethyl acetate (100 mL), then washed with water (2×30 mL). The organic layer was dried with brine and MgSO4, then concentrated in vacuo. Flash column chromatography on silica gel (n-hexanes:ethyl acetate=10:1) of the residue afforded the desired product 48 in 55% yield (142 mg, yellow solid). 1H NMR (400 MHz, CDCl3): 7.70 (d, J=7.2 Hz, 2H), 7.39 (t, J=7.2 Hz, 2H), 7.27 (t, J=7.2 Hz, 1H), 6.97 (d, J=3.6 Hz, 1H), 6.78 (d, J=3.6 Hz, 1H), 6.65 (d, J=1.6 Hz, 1H), 6.43 (d, J=1.6 Hz, 1H), 4.37 (q, J=7.2 Hz, 2H), 1.39 (t, J=7.2 Hz, 3H).

Provenance & Evidence