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

HRID 1478295노트

반응식

HRID 1478295 반응식
[CH:1]1([C:4]([C:8]2[C:13]([CH3:14])=[C:12]([Cl:15])[CH:11]=[CH:10][N:9]=2)=[CH:5][O:6]C)[CH2:3][CH2:2]1.S(=O)(=O)(O)O.[OH-].[Na+]>C(O)(=O)C>[CH3:14][C:13]1[C:8]([CH:4]([CH:1]2[CH2:3][CH2:2]2)[CH:5]=[O:6])=[N:9][CH:10]=[CH:11][C:12]=1[Cl:15]

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 669802244-Chloro-2-(1-cyclopropyl-2-methoxyvinyl)-3-methylpyridine

생성물 1

HCID 186293552-(3-Methyl-4-chloro-pyridin-2-yl)-2-cyclopropyl-acetaldehyde수율 80.3%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A solution of 2-(1-cyclopropyl-2-methoxy-vinyl)-3-methyl-4-chloro-pyridine (6.41 g, 28.7 mmol) in acetic acid (50 mL) was treated with sulfuric acid (6.52 mL, 143 mmol) at room temperature overnight. The reaction mixture was neutralized with 2N NaOH to pH 8-9 extracted with ethyl acetate (2×100 mL). The organic phases were combined, dried, and concentrated. The residue was purified by flash silica column chromatography (hexane/ethyl acetate=2:1) to afford the title compound as a yellow solid (4.83 g, 80%).

후처리

  1. extractionextracted with ethyl acetate (2×100 mL)
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by flash silica column chromatography (hexane/ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-dad976c4da9b4722ae59cd4a96833f13
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403818B2

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