Tributyltin Chloride → 1-Methyl-5-(tributylstannyl)-1H-pyrazole

HRID 216363

反応式

HRID 216363 の反応式
C([N-]C(C)C)(C)C.[Li+].[CH3:9][N:10]1[CH:14]=[CH:13][CH:12]=[N:11]1.Cl[Sn:16]([CH2:25][CH2:26][CH2:27][CH3:28])([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH2:19][CH3:20]>O1CCCC1>[CH3:9][N:10]1[C:14]([Sn:16]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:17][CH2:18][CH2:19][CH3:20])=[CH:13][CH:12]=[N:11]1

参加物

5

反応物 3

HCID 15096Tributyltin ChlorideHCID 702551H-Pyrazole, 1-methyl-HCID 2724682Lithium diisopropylamide

生成物 1

HCID 218674551-Methyl-5-(tributylstannyl)-1H-pyrazole

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

Lithium diisopropylamide (1.5 M in cyclohexane) (9.7 mL, 14.6 mmol) was added to a −78° C. solution of 1-methylpyrazole (1 g, 12.2 mmol) in tetrahydrofuran (15 mL). After stirring at −78° C. for 15 min, chloro-tri-n-butylstannane (3.9 mL, 14.6 mmol) was added dropwise. The reaction mixture was allowed to warm to ambient temperature overnight. The reaction mixture was quenched with saturated aqueous ammonium chloride, diluted with water and extracted with ethyl acetate. The combined organic extracts were dried (magnesium sulfate), filtered and concentrated in vacuo. Chromatography over silica eluting with 0-100 ethyl acetate/hexane afforded 1-methyl-5-(tributylstannyl)-1H-pyrazole.

後処理

  1. temperatureto warm to ambient temperature overnight
  2. customThe reaction mixture was quenched with saturated aqueous ammonium chloride
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-8314bb2997214012b96ae829d21c7b06
出典データセット
uspto-grants-2012_06
特許番号
US08193228B2

関連ノート

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