反応 #596404

反応方程式

2,6-dimethylbromobenzene

diethyl malonate

P(tert-Bu)3

HBF4

K2CO3

→

ethyl 2,6-dimethylphenylacetate

収率 81.0%

反応条件

後処理

1. 1
   その他evacuated
2. 2
   workup.ADDITIONfilled with nitrogen
3. 3
   温度After cooling to room temperature
4. 4
   workup.ADDITIONthe reaction mixture was diluted with ethyl acetate
5. 5
   洗浄The resulting solution was washed successively with 20 ml each of water, saturated aq. NaHCO3 solution and saturated aqueous NaCl solution
6. 6
   乾燥dried over MgSO4
7. 7
   ろ過filtered
8. 8
   濃縮concentrated under reduced pressure
9. 9
   その他Chromatographic purification

実験手順

A dry Schlenk vessel was initially charged with 185 mg [1 mmol] of 2,6-dimethylbromobenzene, 1056 mg [6.6 mmol] of diethyl malonate, 2.88 mg [0.005 mmol] of Pd(dba)2, 3.19 mg [0.011 mmol] of P(tert-Bu)3×HBF4, 207 mg [1.5 mmol] of dried K2CO3 and 150 mg [1.5 mmol] of KHCO3. The reaction vessel was three times evacuated and filled with nitrogen. This was followed by stirring at 160° C. until completion of conversion (8 hours). After cooling to room temperature, the reaction mixture was diluted with ethyl acetate. The resulting solution was washed successively with 20 ml each of water, saturated aq. NaHCO3 solution and saturated aqueous NaCl solution, dried over MgSO4, filtered and concentrated under reduced pressure. Chromatographic purification using silica gel (hexane/ethyl acetate) gave ethyl 2,6-dimethylphenylacetate in a yield of 81% of theory.

出典