Reaktion #1803243

Reaktionsgleichung

4-[(4-bromophenyl)(cycloheptylidene) methyl]-2-chlorophenol

4-[(4-Bromophenyl)(cycloheptylidene)methyl]-2-chlorophenol

ethyl acrylate

triethylamine

TEA

DMF

→

compound 125

Ausbeute 69.0%

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

Ausbeute 69.0%

Lösungsmittel

EtOAc

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe stirred reaction mixture
2. 2
   Temperaturto cool to room temperature
3. 3
   SonstigeThe layers were separated
4. 4
   Waschenthe organic phase was washed with water, brine
5. 5
   Trocknendried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Einengenthe filtrate was concentrated
8. 8
   Sonstigeto give
9. 9
   SonstigeThe crude product was purified by chromatography on a silica gel column
10. 10
    Wascheneluted with a gradient from hexanes to 15% EtOAc

Vorschrift

To a round-bottomed flask were added 4-[(4-bromophenyl)(cycloheptylidene) methyl]-2-chlorophenol (124) (0.32 g, 0.82 mmol), ethyl acrylate (0.90 mL, 8.17 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.060 g, 0.08 mmol), triethylamine (0.60 mL, 4.08 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 over 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 0.23 g (69%) of compound 125 as a colorless viscous oil. 1H NMR (400 MHz, CDCl3): δ 1.33 (t, J=7.1 Hz, 3H), 1.58 (br s, 8H), 2.30 (br s, 4H), 4.25 (q, J=7.1 Hz, 2H), 5.42 (s, 1H), 6.39 (d, J=15.9 Hz, 1H), 6.90-7.00 (m, 2H), 7.10 (d, J=1.8 Hz, 1H), 7.14 (d, J=8.2 Hz, 2H), 7.44 (d, J=8.2 Hz, 2H), 7.65 (d, J=15.9 Hz, 1H). LCMS (ESI): m/z, 433 (M+Na)+, 409 (M−H)−.

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