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

HRID 216363

반응식

HRID 216363 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8314bb2997214012b96ae829d21c7b06
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193228B2

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