反応 #78746

反応方程式

dichloroethane

acetic acid

NaBH(OAc)3

Ethyl 3-aminobenzoate

3-(1,1,2,2-tetrafluoro-ethoxy)benzaldehyde

→

ethyl 3-[[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]amino]benzoate

収率 99.9%

反応条件

後処理

1. 1
   その他quenched with aqueous sodium bicarbonate
2. 2
   抽出extracted with dichloromethane
3. 3
   洗浄The organic layer was washed with brine
4. 4
   乾燥dried over MgSO4
5. 5
   その他evaporated

実験手順

EX-456A) Ethyl 3-aminobenzoate (6.75 mL, 0.045 mol) and 3-(1,1,2,2-tetrafluoro-ethoxy)benzaldehyde (10 g, 45 mmol) were dissolved in 100 mL. of dichloroethane and acetic acid (2.7 mL, 47 mmol), then solid NaBH(OAc)3 (14.3 g, 67 mmol) was added. The mixture was stirred at room temperature for 3 hours, then quenched with aqueous sodium bicarbonate and extracted with dichloromethane. The organic layer was washed with brine, then dried over MgSO4, and evaporated to give 16.7 g (98%) of the desired ethyl 3-[[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]amino]benzoate product as a yellow oil. 1H NMR (CDCl3) δ 1.3 (t, 3H), 4.3 (q, 2H), 4.5 (s, 2H), 6.5 (tt, 1H), 6.9 (d, 1H), 7.1-7.4 (m, 7H).

出典