Reacción #1994298

Ecuación de reacción

sodium

(E)-4-(4-chloro-2-fluoro-3-methoxyphenyl)-but-3-en-2-one

(E)-4-(4-Chloro-2-fluoro-3-methoxyphenyl)-but-3-en-2-one

diethyl oxalate

→

4-chloro-2-fluoro-3-methoxyphenyl-2,4-dioxo-hex-5-enoic acid ethyl ester

Rendimiento 93.0%

(E)-6-(4-Chloro-2-fluoro-3-methoxyphenyl)-2,4-dioxo-hex-5-enoic acid ethyl ester

Rendimiento 93.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowere reacted

Procedimiento

Using the procedure of Example 2, sodium pellets (5.52 g, 0.24 mol), (E)-4-(4-chloro-2-fluoro-3-methoxyphenyl)-but-3-en-2-one (2; 45.73 g, 0.20 mol) and diethyl oxalate (36.54 g, 0.25 mol) were reacted to give (E)-6-(4-chloro-2-fluoro-3-methoxyphenyl-2,4-dioxo-hex-5-enoic acid ethyl ester (5; 61.1 g, 93%) as yellow crystals: mp 67.5-69° C.; 1H NMR (400 MHz, CDCl3) δ 14.71 (s, 1H), 7.78 (d, J=16.1 Hz, 1H), 7.27-7.18 (m, 2H), 6.73 (d, J=16.1 Hz, 1H), 6.54 (s, 1H), 4.38 (q, J=7.1 Hz, 2H), 3.99 (d, J=1.2 Hz, 3H), 1.41 (t, J=7.1 Hz, 3H); HRMS-ESI (m/z): calcd for C15H14ClFNO5, 328.051. found, 328.051.

Fuente