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

HRID 1061442ノート

反応式

HRID 1061442 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]=1OC.S(=O)(=O)(O)O.[CH2:22]1COCC1>>[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[CH3:22]

参加物

4

反応物 3

HCID 1118Sulfuric AcidHCID 8028TetrahydrofuranHCID 682971814-Chloro-2-(1-cyclopropyl-2-methoxyvinyl)-3-methoxy-pyridine

生成物 1

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

実験手順

1.02 g of 2-(4-chloro-3-methoxy-2-pyridyl)-2-cyclopropyl-1-methoxyethene (XI) was dissolved in 10 ml of THF and 10 ml of dilute sulfuric acid was added to the resulting mixture and the resulting mixture 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 0.81 g of 2-(4-chloro-3-methyl-2-pyridyl)-2-cyclopropylethanal (XII).

後処理

  1. concentrationthe resulting mixture was 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-602a27f49da741528ed377148d37d08c
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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