Triethylamine → Ethyl(2E)-3-{4-[(4-hydroxyphenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}-2-propenoate

Participants

Reaction Conditions

Reaction Steps

To a round-bottomed flask were added 4-[(4-bromophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenol (14) (10.2 g, 0.0255 mol), ethyl acrylate (28 mL, 0.255 mol.), dichlorobis(triphenylphosphine) palladium (II) (0.895 g, 1.28 mmol, 5 mol %), Et3N (17.6 mL, 0.128 mol), and DMF (50 mL). The stirred reaction mixture was heated to 110° C. for 18 h under a nitrogen atmosphere. The reaction mixture was allowed to cool to room temperature and then diluted with Et2O (200 mL). The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to give crude product. The crude reaction mixture in DMF was diluted with EtOAc (400 mL), washed with water (2×100 mL), brine (1×100 mL), dried (Na2SO4), filtered, and then concentrated under reduced pressure to afford the crude product as an oil. The crude product was purified by flash chromatography on silica gel with hexanes:EtOAc (19:1 to 1:1) as an eluent to give 8.02 g (75%) of compound 15 as a pale yellow solid. 1H NMR (300 MHz, CDCl3): δ 0.88 (s, 6H), 0.91 (s, 6H), 1.31 (s, 2H), 1.35 (t, J=7.2 Hz, 3H), 1.99 (s, 2H), 2.00 (s, 2H), 4.28 (q, J=7.2 Hz, 2H), 5.35 (broad s, 1H), 6.41 (d, J=16.2 Hz, 1H), 6.77 (d, J=8.4 Hz, 2H), 7.04 (d, J=8.4 Hz, 2H), 7.20 (d, J=8.10 Hz, 1H), 7.44 (d, J=8.40 Hz, 2H), 7.68 (d, J=16.2 Hz, 1H). HRMS (EI) Calcd for C28H34O3: 418.57 (M+). Found: 419.17. Note: Excess ethyl acrylate can be distilled from the reaction mixture before work-up.

Provenance & Evidence