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

HRID 1478295ノート

反応式

HRID 1478295 の反応式
[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]

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 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 80.3%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-dad976c4da9b4722ae59cd4a96833f13
出典データセット
uspto-grants-2016_08
特許番号
US09403818B2

反応ノート

読み込み中…