Sodium Carbonate → 4-[[4'-(Methylsulfonyl)-4-biphenylyl](3,3,5,5-tetramethylcyclohexylidene)methyl]phenol

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Reaction Steps

To a round-bottomed flask were added 4-[(4-bromophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenol (14) (85% pure—contains 15% 3,3,5,5-tetramethylcyclohexanone) (0.117 g, 0.25 mmoL), 4-(methanesulphonyl)benzeneboronic acid (0.165 g, 0.82 mmoL), tetrakis(triphenylphosphine)palladium (0) (0.026 g, 0.023 mmoL), 2 M Na2CO3 (3 mL), and ethylene glycol dimethyl ether (8 mL). The stirred reaction mixture was heated at reflux under a nitrogen atmosphere for 3.5 h. The oil bath was removed and the reaction mixture was allowed to cool at RT. The reaction mixture was transferred to a separatory funnel and partitioned between H2O and EtOAc. The organic phase was separated and the aqueous phase was extracted with EtOAc. The organic extracts were combined, dried over MgSO4, filtered, and the filtrate was concentrated in vacuo to give a brown oil. The crude product was purified by flash chromatography on silica gel using a hexanes:EtOAc gradient (100:0 to 75:25) to give 0.063 g (53%) of compound 163 as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 0.89 (s, 12H), 1.26 (s, 2H), 1.93 (s, 4H), 3.23 (s, 3H), 6.67 (d, J=8.5 Hz, 2H), 6.95 (d, J=8.4 Hz, 2H), 7.25 (d, J=8.2 Hz, 2H), 7.67 (d, J=8.3 Hz, 2H), 7.91 (d, J=8.6 Hz, 2H), 7.95 (d, J=8.6 Hz, 2H), 9.29 (s, 1H). HRMS (ESI) Calcd for C30H33O3S: 473.2150 (M−H)−. Found: 473.2168.

Provenance & Evidence