Hydrochloric Acid → 1-(3-Methoxypyridin-4-yl)ethan-1-one

HRID 4357

반응식

HRID 4357 반응식
[Na].CO[C:4](=[O:13])[C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[O:11][CH3:12].[C:14](OC)(=O)C.Cl.C(=O)(O)[O-].[Na+]>O.CO>[CH3:12][O:11][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:5]=1[C:4](=[O:13])[CH3:14]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 6584Methyl AcetateHCID 516892Sodium BicarbonateHCID 5360545Sodium2회HCID 11400991Methyl 3-methoxyisonicotinate

생성물 1

HCID 128039871-(3-Methoxypyridin-4-yl)ethan-1-one수율 46.3%

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 962Water용매

실험 절차

A dry 50 mL three neck flask fitted with a reflux condenser and internal thermometer was charged with dry methanol (20 mL). Sodium (516 mg, 0.022 mol) was added in portions and after all the sodium had dissolved the methanol was removed by distillation. The resulting sodium methoxide was cooled and a mixture of methyl-3-methoxyisonicotinoate (2.50 g, 0.015 mol) and methyl acetate (6.65 g, 0.090 mol) was added dropwise. The mixture was refluxed for four hours, allowed to cool and dissolved in water (9.0 mL) and concentrated hydrochloric acid (6.0 mL). The resulting mixture was heated to reflux for 2.5 hours, cooled, and basified with 5% sodium bicarbonate. The mixture was extracted with chloroform (4×50 mL) and the combined extracts dried over sodium sulfate, concentrated, and chromatographed through a short column of silica gel to afford 3-methoxy-4-acetylpyridine (1.05 g, 46%). mp. 36°-37° C.

후처리

  1. customwas removed by distillation
  2. temperatureThe resulting sodium methoxide was cooled
  3. additionwas added dropwise
  4. temperatureThe mixture was refluxed for four hours
  5. temperatureto cool
  6. temperatureThe resulting mixture was heated
  7. temperatureto reflux for 2.5 hours
  8. temperaturecooled
  9. extractionThe mixture was extracted with chloroform (4×50 mL)
  10. dry with materialthe combined extracts dried over sodium sulfate
  11. concentrationconcentrated
  12. customchromatographed through a short column of silica gel

출처 및 근거

ORD 기록
ord-d201dac721b14afb8e363997a5e0f3c7
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04725606

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