Cesium carbonate → HCID 86700872, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-(4-(4-bromophenyl)-4-hydroxycyclohexylidene)acetate (190 mg, 0.58 mmol) in acetonitrile (7 mL) was added Cs2CO3 (381 mg, 1.17 mmol) and the reaction was let stir in a 50° C. oil bath for 24 h. The resulting reaction mixture was diluted with ethyl acetate and washed with water, followed by a saturated aqueous NaCl solution. The organic phase was dried over MgSO4, filtered and concentrated by rotary evaporation in vacuo to afford 188 mg of crude orange film. The crude material was purified by column chromatography (24 g silica gel, 0-40% EtOAc:Hept, monitor 230 nm) to afford 64 mg (34%) of the title compound as a colorless film that solidified upon standing. 1H NMR (400 MHz, DMSO-d6): δ ppm 1.56-1.81 (m, 4H), 1.85-1.97 (m, 2H), 2.14 (td, J=9.9, 3.9 Hz, 2H), 2.92 (s, 2H), 3.63 (s, 3H), 7.32 (d, J=8.6 Hz, 2H), 7.53 (d, J=8.6 Hz, 2H). 13C NMR (100 MHz, DMSO-d6): δ ppm 170.3, 142.0, 130.9, 127.1, 119.8, 86.0, 83.2, 51.3, 37.6, 35.4 (additional signal likely hidden under DMSO solvent signal). ESI-MS m/z: 327.0 [M+H]+, retention time 1.55 min (condition E).

Provenance & Evidence