反応 #2383808

反応方程式

water

1-morpholino-1-cyclohexene

2-nitroethylacetate

HCl

Water

→

2-(2-nitroethyl)cyclohexanone

溶媒

acetonitrile

EtOAc

反応条件

後処理

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
   その他The dark red reaction mixture
4. 4
   その他the layers separated
5. 5
   抽出The light orange water layer (bottom) was extracted again with 50 mL of EtOAc
6. 6
   洗浄The combined EtOAc layers were washed with saturated brine (2×85 mL)
7. 7
   乾燥dried (MgSO4)
8. 8
   ろ過filtered
9. 9
   濃縮concentrated

実験手順

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.

出典