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Ethyl Acetate → (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylonitrile

HRID 546654
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HRID 546654 반응식
O.[OH-].[Li+].[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[N:14]1[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]1)[CH:9]=O.[C:20]([CH2:22]P(=O)(OCC)OCC)#[N:21].C(OCC)(=O)C>C1COCC1.O>[CH3:4][O:5][C:6]1[CH:7]=[C:8](/[CH:9]=[CH:22]/[C:20]#[N:21])[CH:11]=[CH:12][C:13]=1[N:14]1[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 75676Diethyl (cyanomethyl)phosphonateHCID 168937Lithium hydroxide, monohydrateHCID 272824453-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde

생성물 1

HCID 66839440(E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylonitrile

시약·촉매·용매 2

HCID 962
Water
용매
HCID 8028Tetrahydrofuran용매

실험 절차

A lithium hydroxide monohydrate powder (2.23 g) was added to a suspension of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (CAS No. 870837-18-6, 10 g) and diethyl cyanomethylphosphonate (8.2 g) in THF (50 ml) under ice-cooling, and the reaction solution was stirred at the same temperature for one hour. Ethyl acetate (200 mL) and water were added to the reaction solution, and the organic layer was separated. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and then filtered through a silica gel pad (carrier: Chromatorex™ NH). The filtrate was concentrated under reduced pressure. The resulting residue was crystallized from ethyl acetate and hexane, and the crystals were collected by filtration. The resulting crystals were dried under reduced pressure to obtain 7.49 g of the title compound. The property values of the compound are as follows.

후처리

  1. customthe organic layer was separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered through a silica gel pad (carrier: Chromatorex™ NH)
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was crystallized from ethyl acetate and hexane
  7. filtrationthe crystals were collected by filtration
  8. customThe resulting crystals were dried under reduced pressure

출처 및 근거

ORD 기록
ord-43dd771e102246d78d7403d3930fdc50
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07935815B2

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