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

HRID 216363Notes

Reaction equation

HRID 216363 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8314bb2997214012b96ae829d21c7b06
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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