Nitronium tetrafluoroborate → Methyl 3-(4-nitrophenyl)-1-adamantaneacetate

HRID 21683

反応式

HRID 21683 の反応式
[C:1]1([C:7]23[CH2:16][CH:11]4[CH2:12][CH:13]([CH2:15][C:9]([CH2:17][C:18]([O:20][CH3:21])=[O:19])([CH2:10]4)[CH2:8]2)[CH2:14]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[B-](F)(F)F.[O:27]=[N+:28]=[O:29]>C(#N)C>[N+:28]([C:4]1[CH:3]=[CH:2][C:1]([C:7]23[CH2:16][CH:11]4[CH2:12][CH:13]([CH2:15][C:9]([CH2:17][C:18]([O:20][CH3:21])=[O:19])([CH2:10]4)[CH2:8]2)[CH2:14]3)=[CH:6][CH:5]=1)([O-:29])=[O:27]

参加物

4

反応物 2

HCID 11073463Nitronium tetrafluoroborateHCID 53665692Methyl 3-phenyl-1-adamantaneacetate

生成物 1

HCID 2843871Methyl 3-(4-nitrophenyl)-1-adamantaneacetate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

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) yielded 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.

後処理

  1. temperaturecooled in an ice bath
  2. stirringThe reaction was stirred for 45 minutes
  3. additionafter the addition
  4. filtrationThe resulting solid was collected by filtration
  5. customdried in vacuo

出典と根拠

ORDレコード
ord-f83bcdbd75e34ea5961abfa57d12f2ab
出典データセット
uspto-grants-1995_06
特許番号
US05424414

関連ノート

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