反応 #80262

反応方程式

Methyl 3-phenyl-1-adamantaneacetate

Nitronium tetrafluoroborate

→

methyl 3-(4-nitrophenyl)-1-adamantaneacetate

溶媒

acetonitrile

acetonitrile

反応条件

後処理

1. 1
   温度cooled in an ice bath
2. 2
   workup.STIRRINGThe reaction was stirred for 45 minutes
3. 3
   workup.ADDITIONafter the addition
4. 4
   ろ過The resulting solid was collected by filtration
5. 5
   その他dried in vacuo

実験手順

Methyl 3-phenyl-1-adamantaneacetate, example 1, (78.8 g) was dissolved in acetonitrile (800 mL) and cooled in an ice bath while stirring under a nitrogen atmosphere. Nitronium tetrafluoroborate (40.8 g) in acetonitrile (800 mL) was added dropwise over 45 minutes. The reaction was stirred for 45 minutes after the addition, then poured into ice (985 g). The resulting solid was collected by filtration and dried in vacuo to give methyl 3-(4-nitrophenyl)-1-adamantaneacetate (55.9 g). Mass spectrum: (M+NH4)+ @347. Extraction of the aqueous phase with t-butyl methyl ether (2×800 mL) yeilded additional material including the lesser products, methyl 3-(2-nitrophenyl)-1-adamantaneacetate; Mass spectrum: (M+NH4)+ @347 and methyl 3-(2,4-dinitrophenyl)-1-adamantaneacetate; Mass spectrum: (M+NH4)+ @392.

出典