반응 #316396

반응 방정식

4-[(4-bromophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]-2-chlorophenol

4-[(4-Bromophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]-2-chlorophenol

ethyl acrylate

Et3N

DMF

→

compound 128

수율 66.0%

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

수율 66.0%

용매

EtOAc

water

반응 조건

후처리

1. 1
   기타The stirred reaction mixture
2. 2
   온도to cool to room temperature
3. 3
   기타The layers were separated
4. 4
   세척the organic phase was washed with water, brine
5. 5
   건조dried (Na2SO4)
6. 6
   여과filtered
7. 7
   농축the filtrate was concentrated
8. 8
   기타to give
9. 9
   기타The crude product was purified by chromatography on a silica gel column
10. 10
    세척eluted with a gradient from hexanes to 15% EtOAc

실험 절차

To a round-bottomed flask were added 4-[(4-bromophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]-2-chlorophenol (127) (0.38 g, 0.88 mmol), ethyl acrylate (0.96 mL, 8.80 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.062 g, 0.09 mmol), Et3N (0.61 mL, 4.38 mmol) and DMF (10 mL). The stirred reaction mixture was heated overnight at 100° C. under a nitrogen atmosphere. The reaction mixture was allowed to cool to room temperature and transferred to a separatory funnel with the aid of water and EtOAc (100 mL). The layers were separated and the organic phase was washed with water, brine, dried (Na2SO4), filtered, and the filtrate was concentrated to give reddish brown oil. The crude product was purified by chromatography on a silica gel column eluted with a gradient from hexanes to 15% EtOAc:hexanes to give 0.26 g (66%) of compound 128 as a yellow viscous oil. 1H NMR (400 MHz, CDCl3): δ 0.92 (s, 6H), 0.94 (s, 6H), 1.30 (s, 2H), 1.33 (t, J=7.1 Hz, 3H), 1.96 (s, 2H), 1.97 (s, 2H), 4.25 (q, J=7.1 Hz, 2H), 5.43 (s, 1H), 6.39 (d, J=15.9 Hz, 1H), 6.90-7.00 (m, 2H), 7.11 (d, J=1.8 Hz, 1H), 7.16 (d, J=8.1 Hz, 2H), 7.44 (d, J=8.1 Hz, 2H), 7.65 (d, J=15.9 Hz, 1H). LCMS (ESI): m/z, 453 (M+H)+, 451 (M−H)−.

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