Acetonitrile → 4-(3,4-Dimethoxyphenyl)-3-oxo-butyronitrile

HRID 506148

반응식

HRID 506148 반응식
C([Li])CCC.[C:6](#[N:8])[CH3:7].C[O:10][C:11](=O)[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=1.[Cl-].[NH4+]>C1COCC1>[CH3:22][O:21][C:15]1[CH:14]=[C:13]([CH2:12][C:11](=[O:10])[CH2:7][C:6]#[N:8])[CH:18]=[CH:17][C:16]=1[O:19][CH3:20]

참가 물질

6

반응물 4

HCID 6342AcetonitrileHCID 25517Ammonium ChlorideHCID 85213Benzeneacetic acid, 3,4-dimethoxy-, methyl esterHCID 178418339Butyllithium

생성물 1

HCID 125197054-(3,4-Dimethoxyphenyl)-3-oxo-butyronitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

To a 1.0 L three-necked round-bottomed flask was added 50 mL of THF and the reaction mixture was cooled to −78° C. Butyl lithium (BuLi, 1.6 M, 14.4 mL, 23 mmol) was added dropwise keeping the temperature below −70° C. Acetonitrile (1.3 mL, 25 mmol) in 30 mL of THF was added dropwise to the flask amidst stirring and cooling. After 2 hours (h) of stirring, (3,4-dimethoxyphenyl)acetic acid methyl ester (2.3 g, 11 mmol) was added to the resulting white colloidal mixture in the flask. The reaction mixture was stirred for a further 2 h, followed by the addition of saturated ammonium chloride solution (NH4Cl, 75 mL) at −78° C. The organic layer was separated, dried with sodium sulfate (Na2SO4), filtered to remove the drying agent and evaporated to dryness to give the crude product. This crude product was purified by silica gel column chromatography, eluting with 30-70% ethyl acetate (EtOAc) in hexanes to yield 4-(3,4-dimethoxyphenyl)-3-oxo-butyronitrile in the form of a solidifying amber oil, 1.8 g (75%).

후처리

  1. customthe temperature below −70° C
  2. temperaturecooling
  3. stirringAfter 2 hours (h) of stirring
  4. stirringThe reaction mixture was stirred for a further 2 h
  5. customThe organic layer was separated
  6. dry with materialdried with sodium sulfate (Na2SO4)
  7. filtrationfiltered
  8. customto remove the drying agent
  9. customevaporated to dryness
  10. customto give the crude product
  11. customThis crude product was purified by silica gel column chromatography
  12. washeluting with 30-70% ethyl acetate (EtOAc) in hexanes

출처 및 근거

ORD 기록
ord-18ffdcc372ca4db49416ce42c4107be2
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781591B2

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