Reaktion #43289

Reaktionsgleichung

triethylamine

t-butanol

1-(4-propoxyphenyl) ethanone

2-bromo-1-(2-chlorophenyl) ethanone

→

light yellow solid

Ausbeute 37.4%

1-(2-Chlorophenyl)-4-(4-propoxyphenyl)-butane-1,4-dione

Ausbeute 37.4%

Lösungsmittel

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvents were removed at reduced pressure
2. 2
   workup.ADDITIONthe residue added to 100 mL of water
3. 3
   ExtraktionThe aqueous phase was extracted with ethyl acetate (200 mL) twice
4. 4
   WaschenThe combined organic layers were washed with water (150 mL), saturated brine
5. 5
   Trocknendried (Na2SO4)
6. 6
   Sonstigethe solvents removed at reduced pressure

Vorschrift

To a solution of 11.7 gm (85.6 mmol) of fused ZnCl2 in 20 mL of benzene was 10 added 8.50 mL (64 mmol) of triethylamine and 6.12 mL (64 mmol) of dry t-butanol. After dissolution at room temperature 11.45 gm (64 mmol) of 1-(4-propoxyphenyl) ethanone 100 and 10.0 gm (42.8 mmol) of 2-bromo-1-(2-chlorophenyl) ethanone 99. The mixture was allowed to stir at room temperature for 6 days. The solvents were removed at reduced pressure and the residue added to 100 mL of water. The aqueous phase was extracted with ethyl acetate (200 mL) twice. The combined organic layers were washed with water (150 mL), saturated brine, dried (Na2SO4) and the solvents removed at reduced pressure. Column chromatography of the residue using 2%-4%-8% ethyl acetate-hexanes yielded 5.3 gm (37%) of a light yellow solid. This was recrystallized from hot hexanes-ethyl acetate. 1H NMR (400 MHz, CDCl3) δ: 1.04 (t, 3H, J=7.42 Hz), 1.82 (m, 2H), 3.36 (m, 2H), 3.42 (m, 2H), 3.98 (t, 2H, J=6.5 Hz), 6.92 (d, 2H J=8.9 Hz), 7.38 (m, 3H), 7.64 (m, 1H), 7.97 (m, 2H).

Quelle