Ethyl Acetate → HCID 178424789、化合物

HRID 1958859ノート

反応式

HRID 1958859 の反応式
[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([CH3:15])=[C:8]([CH2:12][C:13]#[N:14])[CH:9]=[CH:10][CH:11]=1.[N-:21]=[N+:22]=[N-:23].[Na+].[Cl-].[NH4+].C(OCC)(=O)C>CN(C=O)C.CCCCCC>[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([CH3:15])=[C:8]([CH:9]=[CH:10][CH:11]=1)[CH2:12][C:13]1[NH:23][N:22]=[N:21][N:14]=1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 669591112-(3-(2,6-Dimethylbenzyloxy)-2-methylphenyl)acetonitrile

生成物 1

HCID 178424789HCID 178424789、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8058Hexane溶媒

反応条件

温度
90 °C

実験手順

A mixture of 2-(3-(2,6-Dimethylbenzyloxy)-2-methylphenyl)acetonitrile (Step F, 2.70 g, 10.19 mmol), sodium azide (0.795 g, 12.23 mmol) and ammonium chloride (0.653 g, 12.22 mmol) in dry DMF (20 ml) was heated under argon at 90° C. for 16 hours or until all the starting material is consumed, the reaction mixture was cooled, diluted with water and extracted with EtOAc (30 ml×4). The combined organic layer was washed with brine, dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (chloroform:methanol 92.5:7.5) to give semi solid product. The semi solid was stirred with 1:2 ethyl acetate:hexane (15 ml) for 10 minutes, and filtered to give product as a white solid.

後処理

  1. customis consumed
  2. temperaturethe reaction mixture was cooled
  3. additiondiluted with water
  4. extractionextracted with EtOAc (30 ml×4)
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by flash chromatography on a silica gel column (chloroform:methanol 92.5:7.5)
  10. customto give semi solid product
  11. filtrationfiltered
  12. customto give product as a white solid

出典と根拠

ORDレコード
ord-271a7fe085d24c3bb35f1a2273bd4f1f
出典データセット
uspto-grants-2013_04
特許番号
US08410154B2

反応ノート

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