Reaktion #172137

Reaktionsgleichung

ethyl 2-(2-bromophenyl)acetate

t-butyl acrylate

dicyclohexylmethylamine

tri-tert-butylphosphine

→

title compound

(E)-tert-Butyl 3-(2-(2-ethoxy-2-oxoethyl)phenyl)acrylate

Lösungsmittel

dioxane

Ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe mixture was filtered through diatomaceous earth
2. 2
   EinengenThe filtrate was concentrated
3. 3
   Sonstigepurified by silica gel column chromatography
4. 4
   Wascheneluting with hexanes and ethyl acetate (10:1)

Vorschrift

To a mixture of ethyl 2-(2-bromophenyl)acetate (0.97 g, 4 mmol), t-butyl acrylate (0.51 g, 4 mmol), tris(dibenzylideneacetone)dipalladium(0) (91 mg, 0.1 mmol), dicyclohexylmethylamine (0.98 g, 5 mmol) in dioxane (5 mL) was added tri-tert-butylphosphine (0.2 mL, 1 N in toluene, 0.2 mmol). The mixture was heated at 70° C. for 30 minutes under N2. Ethyl acetate was added, and the mixture was filtered through diatomaceous earth. The filtrate was concentrated and purified by silica gel column chromatography eluting with hexanes and ethyl acetate (10:1) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.79 (m, 1H), 7.72 (d, J=15.6 Hz, 1H), 7.34 (m, 3H), 6.40 (d, J=15.7 Hz, 1H), 4.06 (q, J=7.2 Hz, 2H), 3.84 (s, 2H), 1.48 (s, 9H), and 1.17 (t, J=2 Hz, 3H).

Quelle