反应 #2383796

反应方程式

acetic acid

2-(isopropylamino)ethanol

2-fluoro-5-nitrobenzaldehyde

sodium triacetoxyborohydride

water

→

2-[(2-Fluoro-5-nitrobenzyl)(isopropyl)amino]ethanol oxalate

溶剂

THF

反应条件

后处理

1. 1
   洗涤washed with methylene chloride (250 ml)
2. 2
   萃取extracted with methylene chloride (3×250 ml)
3. 3
   干燥The extracts were dried with magnesium sulfate
4. 4
   过滤filtered
5. 5
   浓缩concentrated to an oil
6. 6
   workup.DISSOLUTIONThe oil was dissolved in 95% ethanol
7. 7
   workup.ADDITIONtreated with isopropanol-oxalic acid
8. 8
   过滤The oxalate salt was collected by filtration (31.2 g, 20%), m.p. 106-107° C.

实验过程

To acetic acid (25.76 ml, 450 mmol) and 2-(isopropylamino)ethanol (51.76 ml, 450 mmol) in dry THF (750 ml) at 0° C. was added 2-fluoro-5-nitrobenzaldehyde (75.88 g, 450 mmol) and sodium triacetoxyborohydride (141.99 g, 670 mmol) portionwise. The reaction was allowed to warm to room temperature and was stirred for 3 h. The mixture was taken up in acidic water and washed with methylene chloride (250 ml), made basic with 50% sodium hydroxide (150 ml) and extracted with methylene chloride (3×250 ml). The extracts were dried with magnesium sulfate, filtered, and concentrated to an oil. The oil was dissolved in 95% ethanol and treated with isopropanol-oxalic acid. The oxalate salt was collected by filtration (31.2 g, 20%), m.p. 106-107° C.

来源