反応 #219864

反応方程式

Compound 1E

2-Chloro-4-Iodo-3-methylbenzonitrile

diethyl malonate

NaH

→

title compound

収率 82.5%

Diethyl 2-(3-chloro-4-cyano-2-methylphenyl)malonate

収率 82.5%

溶媒

dioxane

反応条件

後処理

1. 1
   その他To a pressure reaction flask
2. 2
   その他sealed
3. 3
   温度The reaction was cooled to RT
4. 4
   ろ過filtered through a pad of celite
5. 5
   洗浄The celite pad was washed with EtOAc
6. 6
   洗浄The organics were washed twice with water
7. 7
   乾燥dried over Na2SO4
8. 8
   ろ過filtered
9. 9
   濃縮concentrated
10. 10
    その他Purification by flash chromatography (silica gel, 110 g ISCO, 10% EtOAc in hexane)

実験手順

To a pressure reaction flask containing diethyl malonate (4.1 mL, 27 mmol) in 50 mL of anhydrous dioxane was added NaH (1.1 g, 27.5 mmol, ˜60% in mineral oil) in several portions at RT, and stirred for 30 min. Compound 1E (2.5 g, 9 mmol) and CuI (5.1 g, 26.8 mmol) were added, sealed and heated at 100° C. for 3 days. The reaction was cooled to RT and filtered through a pad of celite. The celite pad was washed with EtOAc. The organics were washed twice with water, dried over Na2SO4, filtered and concentrated. Purification by flash chromatography (silica gel, 110 g ISCO, 10% EtOAc in hexane) gave the title compound (2.3 g).

出典