تفاعل #172137

معادلة التفاعل

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

المذيبات

dioxane

Ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   ترشيحthe mixture was filtered through diatomaceous earth
2. 2
   تركيزThe filtrate was concentrated
3. 3
   أخرىpurified by silica gel column chromatography
4. 4
   غسيلeluting with hexanes and ethyl acetate (10:1)

الإجراء التجريبي

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).

المصدر