Iodoethane → 4-(1-Cyano-1-ethylpropyl)benzonitrile

HRID 419977노트

반응식

HRID 419977 반응식
[C:1]([CH2:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)#[N:2].[CH2:12](I)[CH3:13].[H-].[Na+].[CH3:17][CH2:18]OC(C)=O>CCCCCCC.O.CN(C=O)C>[C:1]([C:3]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)([CH2:12][CH3:13])[CH2:17][CH3:18])#[N:2]

참가 물질

8

반응물 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 1366864-Cyanophenylacetonitrile

생성물 1

HCID 582984684-(1-Cyano-1-ethylpropyl)benzonitrile

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8900Heptane용매

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온도
0 °C

실험 절차

4-Cyanomethylbenzonitrile (1.02 g, 7.18 mmol) and ethyl iodide (2.25 g, 14.4 mmol) are added to DMF (20.0 mL), and the resulting solution is cooled to 0° C. NaH (576 mg, 14.4 mmol) is added in portions. The mixture is warmed to room temperature and then stirred for 3 hours. Water (100 mL) is added, and the aqueous phase is extracted with EtOAc (4 times with 50.0 mL). The combined organic phases are dried with MgSO4, filtered and concentrated on the rotovaporator. The product is purified by Combi-Flash silica gel chromatography, eluting with mixtures of heptane and EtOAc (100/0 to 70/30), (936 mg, 5.51 mmol, 77%). 1H NMR (400 MHz, DMSO-D6) δ ppm 0.77 (t, J=7.42 Hz, 6H) 1.89-2.14 (m, 4H) 7.64 (d, J=8.40 Hz, 2H) 7.92 (d, J=8.59 Hz, 2H).

후처리

  1. temperatureThe mixture is warmed to room temperature
  2. extractionthe aqueous phase is extracted with EtOAc (4 times with 50.0 mL)
  3. dry with materialThe combined organic phases are dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated on the rotovaporator
  6. customThe product is purified by Combi-Flash silica gel chromatography

출처 및 근거

ORD 기록
ord-10ba435c4cd842f48206c1b80667c273
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093402B2

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