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

HRID 419977ノート

反応式

HRID 419977 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8900Heptane溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-10ba435c4cd842f48206c1b80667c273
出典データセット
uspto-grants-2012_01
特許番号
US08093402B2

反応ノート

読み込み中…