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

HRID 51984

반응식

HRID 51984 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2a97706acabd438eb775c9adf442792f
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616505

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