反応 #79578

反応方程式

Sodium triacetoxyborohydride

Acetic acid

p-anisaldehyde

ethanolamine

→

title compound

2-[(4-Methoxybenzyl)amino]ethanol

溶媒

methanol

反応条件

後処理

1. 1
   workup.ADDITIONonce addition
2. 2
   濃縮The mixture was concentrated under reduced pressure
3. 3
   抽出extracted with dichloromethane (10×300 ml)
4. 4
   その他The combined extracts were evaporated
5. 5
   その他the crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol (98:2 to 90:10)

実験手順

Acetic acid (ca. 150 ml) was added to a solution of p-anisaldehyde (58.2 g, 0.42 mol) and ethanolamine (152 ml, 2.52 mol) in methanol (1L), to achieve a pH of 6. Sodium triacetoxyborohydride (100 g, 0.47 mol) was added portionwise, and once addition was complete, the mixture was stirred at room temperature for 72 hours. The mixture was concentrated under reduced pressure, basified using 1N sodium hydroxide solution and extracted with dichloromethane (10×300 ml). The combined extracts were evaporated and the crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol (98:2 to 90:10) to afford the title compound, 42 g. 1H-NMR (CDCl3, 400 MHz) δ: 2.78 (t, 2H), 3.62 (t, 2H), 3.75 (m, 5H), 4.24 (s, 2H), 6.81 (d, 2H), 7.22 (d, 2H). LRMS: m/z (ES+) 182 [MH+].

出典