反应 #2383808

反应方程式

water

1-morpholino-1-cyclohexene

2-nitroethylacetate

HCl

Water

→

2-(2-nitroethyl)cyclohexanone

溶剂

acetonitrile

EtOAc

反应条件

后处理

1. 1
   workup.STIRRINGThe red solution was then stirred at ambient temperature under an N2 atmosphere overnight
2. 2
   workup.ADDITIONdropped to 27° C. by the end of the addition
3. 3
   其他The dark red reaction mixture
4. 4
   其他the layers separated
5. 5
   萃取The light orange water layer (bottom) was extracted again with 50 mL of EtOAc
6. 6
   洗涤The combined EtOAc layers were washed with saturated brine (2×85 mL)
7. 7
   干燥dried (MgSO4)
8. 8
   过滤filtered
9. 9
   浓缩concentrated

实验过程

To a solution of 1-morpholino-1-cyclohexene (51 g; 300 mmol) in 120 mL anhydrous acetonitrile at 0-4° C. was added the 2-nitroethylacetate product of Example 2a (37.8 g, 293 mmol) dropwise. The resulting red solution was stirred under N2 atmosphere in an ice bath for 2½ hrs. The red solution was then stirred at ambient temperature under an N2 atmosphere overnight. Water (100 mL) was added to the red solution over a 10-15 minute period. The temperature rose from 20 to 29° C. with the first 200 mL of water, but then dropped to 27° C. by the end of the addition. This was then acidified with aqueous HCl. The dark red reaction mixture was diluted with 85 mL of EtOAc and the layers separated. The light orange water layer (bottom) was extracted again with 50 mL of EtOAc. The combined EtOAc layers were washed with saturated brine (2×85 mL), dried (MgSO4), filtered and concentrated to afford 45 g of 2-(2-nitroethyl)cyclohexanone as a red oil.

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