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

HRID 1061442노트

반응식

HRID 1061442 반응식
[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]

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-602a27f49da741528ed377148d37d08c
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06525066B2

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