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

HRID 4357

反応式

HRID 4357 の反応式
[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]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 6584Methyl AcetateHCID 516892Sodium BicarbonateHCID 5360545Sodium2 回HCID 11400991Methyl 3-methoxyisonicotinate

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d201dac721b14afb8e363997a5e0f3c7
出典データセット
uspto-grants-1988_02
特許番号
US04725606

関連ノート

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