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

HRID 1478294노트

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HRID 1478294 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
40 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-70627d9de87643d5a0523125e04d7cad
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403818B2

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