Реакция #172137

Уравнение реакции

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

Растворители

dioxane

Ethyl acetate

Условия реакции

Обработка

1. 1
   Фильтрацияthe mixture was filtered through diatomaceous earth
2. 2
   КонцентрированиеThe filtrate was concentrated
3. 3
   Другоеpurified by silica gel column chromatography
4. 4
   Промывкаeluting with hexanes and ethyl acetate (10:1)

Методика

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).

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