Sulfuric Acid → 2-(3-Methyl-4-chloro-pyridin-2-yl)-2-cyclopropyl-acetaldehyde

HRID 1061435ノート

反応式

HRID 1061435 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([CH:12]2[CH2:14][CH2:13]2)=[CH:9][O:10]C)[C:3]=1[CH3:15].S(=O)(=O)(O)O>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]([CH:12]2[CH2:14][CH2:13]2)[CH:9]=[O:10])[C:3]=1[CH3:15]

参加物

4

反応物 2

HCID 1118Sulfuric AcidHCID 669802244-Chloro-2-(1-cyclopropyl-2-methoxyvinyl)-3-methylpyridine

生成物 1

HCID 186293552-(3-Methyl-4-chloro-pyridin-2-yl)-2-cyclopropyl-acetaldehyde収率 84.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

1.66 g of 2-(4-chloro-3-methyl-2-pyridyl)-2-cyclopropyl-1-methoxyethene (XI) was dissolved in 16 ml of THF and 16 ml of dilute sulfuric acid was added to the resulting mixture, which was concentrated at 50° C. under reduced pressure. The resulting mixture was poured into water and neutralized with saturated sodium bicarbonate solution, and thereafter, extracted with chloroform. The resulting organic layer was washed with saturated salt water, and thereafter, dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1) to obtain 1.31 g of 2-(4-chloro-3-methyl-2-pyridyl)-2-cyclopropylethanal (XII).

後処理

  1. concentrationwas concentrated at 50° C. under reduced pressure
  2. additionThe resulting mixture was poured into water and neutralized with saturated sodium bicarbonate solution
  3. extractionextracted with chloroform
  4. washThe resulting organic layer was washed with saturated salt water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-f7429e4dd17e47b083f8f0506e884861
出典データセット
uspto-grants-2003_02
特許番号
US06525066B2

反応ノート

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