Sodium hydride → 4-Chloro-2-(1-cyclopropyl-2-methoxyvinyl)-3-methylpyridine

HRID 1478294ノート

反応式

HRID 1478294 の反応式
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[H-].[Na+].[CH3:26][C:27]1[C:28]([C:34]([CH:36]2[CH2:38][CH2:37]2)=O)=[N:29][CH:30]=[CH:31][C:32]=1[Cl:33]>C1COCC1>[CH:36]1([C:34]([C:28]2[C:27]([CH3:26])=[C:32]([Cl:33])[CH:31]=[CH:30][N:29]=2)=[CH:2][O:3][CH3:4])[CH2:38][CH2:37]1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 66980317(4-Chloro-3-methyl-2-pyridyl)cyclopropylketone

生成物 1

HCID 669802244-Chloro-2-(1-cyclopropyl-2-methoxyvinyl)-3-methylpyridine収率 82.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
40 °C

実験手順

A solution of methoxymethyl triphenylphosphonium chloride (17.9 g, 52.3 mmol) in dry THF (80 mL) was treated with NaH (2.79 g, 69.8 mmol) at 0° C. for 3 h. To this mixture was added a solution of (3-methyl-4-chloro-pyridin-2-yl)-cyclopropyl-methanone (6.82 g, 34.9 mmol) in dry THF (20 mL). The reaction mixture was heated at 40° C. overnight. The reaction mixture was cooled down to room temperature and filtered. The filtrate was concentrated to dryness. The residue was purified by flash silica column chromatography (hexane:ethyl acetate, 3:1) to afford the title compound (6.41 g, 82%).

後処理

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated to dryness
  4. customThe residue was purified by flash silica column chromatography (hexane:ethyl acetate, 3:1)

出典と根拠

ORDレコード
ord-70627d9de87643d5a0523125e04d7cad
出典データセット
uspto-grants-2016_08
特許番号
US09403818B2

反応ノート

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