Water → 3-(2-Pyridyl)acrylonitrile

HRID 748403

반응식

HRID 748403 반응식
[H-].[Na+].[C:3]([CH2:5][CH2:6]P(=O)(OCC)OCC)#[N:4].[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1C=O.O>O1CCCC1>[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH:6]=[CH:5][C:3]#[N:4]

참가 물질

6

반응물 4

HCID 962WaterHCID 142732-PyridinecarboxaldehydeHCID 24758Sodium hydrideHCID 82369Diethyl (2-cyanoethyl)phosphonate

생성물 1

HCID 545488663-(2-Pyridyl)acrylonitrile수율 15.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

Sodium hydride (ca. 60%, 1.0 g, 28.1 mmol) was suspended in tetrahydrofuran (12 ml), and a solution of diethyl cyanoethylphosphonate (4.7 g, 26.8 mmol) in tetrahydrofuran (12 ml) was added thereto under ice cooling condition. The reaction mixture was stirred for 1 hr. A solution of 2-pyridinecarbaldehyde (2.7 g, 25.0 mmol) in tetrahydrofuran (10 ml) was added to the mixture, and the mixture was stirred at 0° C. to room temperature for 6 hrs. The reaction mixture was combined with water under ice cooling condition, concentrated to the half amount and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated, and the residue was subjected to a silica gel (100 g) column chromatography. The fractions eluted with hexane-ethyl acetate (2:1, v/v) were collected and concentrated to give Z-form of the titled compound (0.50 g, 15%). And simultaneously, the fractions eluted with hexane-ethyl acetate (3:2, v/v) were collected and concentrated to give E-form of the titled compound.

후처리

  1. stirringthe mixture was stirred at 0° C. to room temperature for 6 hrs
  2. concentrationconcentrated to the half amount
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated
  7. washThe fractions eluted with hexane-ethyl acetate (2:1, v/v)
  8. customwere collected
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-418c18bd680542b7aec45ea70e8ee736
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07399759B2

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