Ethyl Acetate → Amino-5-[2-(4-cyanophenyl)ethoxy]-2-methylbenzene

HRID 1791857노트

반응식

HRID 1791857 반응식
[BH4-].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([N+:21]([O-])=O)[CH:15]=2)=[CH:7][CH:6]=1)#[N:4].CCOC(C)=O>CCO.S([O-])([O-])(=O)=O.[Cu+2]>[NH2:21][C:16]1[CH:15]=[C:14]([O:13][CH2:12][CH2:11][C:8]2[CH:7]=[CH:6][C:5]([C:3]#[N:4])=[CH:10][CH:9]=2)[CH:19]=[CH:18][C:17]=1[CH3:20]

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 22033464[2-(4-Cyanophenyl)ethoxy]-4-methyl-3-nitrobenzene

생성물 1

HCID 22033532Amino-5-[2-(4-cyanophenyl)ethoxy]-2-methylbenzene수율 26%

시약·촉매·용매 2

HCID 24462Copper Sulfate촉매HCID 702Ethanol용매

실험 절차

Sodium borohydride (0.127 g; 3.35 mmol) was added in portions to a cold suspension (ice:water temperature) of [2-(4-cyanophenyl)ethoxy]-4-methyl-3-nitrobenzene (0.19 g; 0.67 mmol; from step (i) above) and aqueous copper sulfate (1.34 mL; 1 M; 1.34 mmol) in EtOH (5 mL) over five minutes. The temperature was allowed to rise to ambient and the stirring continued for 30 minutes. Addition of EtOAc (50 mL) and filtration through Celite afforded a clear solution that was washed with water, dried (K3CO3) and concentrated in vacuo. Flash chromatography (SiO2; toluene:EtOAc (10:1)) afforded 0.044 g (26%) of the sub-title compound as a white solid.

후처리

  1. customafforded a clear solution that
  2. washwas washed with water
  3. customdried (K3CO3)
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-97967a60623a4f7b94a70e73c45afd80
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074820B2

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