Tributyltin Chloride → HCID 10937203, compound

HRID 356594Notes

Reaction equation

HRID 356594 reaction equation
I[C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.C([Li])(C)(C)C.[CH2:12]([Sn:16](Cl)([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][CH2:14][CH3:15]>C1COCC1>[CH2:21]([Sn:16]([CH2:12][CH2:13][CH2:14][CH3:15])([CH2:17][CH2:18][CH2:19][CH3:20])[C:2]1[CH:3]=[N:4][NH:5][CH:6]=1)[CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 770224-IodopyrazoleHCID 178418306HCID 178418306, compound

Product 1

HCID 10937203HCID 10937203, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-iodopyrazole (0.964 g) in THF (20 mL) under nitrogen and cooled to -60° C. is added t-butyllithium (1.7M in pentane, 9 mL) at such a rate that the temperature remained below -55° C. Tributyltin chloride (1.2 mL) was then added and the mixture was allowed to warm to room temperature. The reaction was quenched with water, diluted with ethyl acetate, washed with water, dried (anhyd Na2SO4), filtered, and evaporated. Chromatography of the residue over silica gel (ethyl acetate/hexane) gave 4-(tributylstannyl)pyrazole (0.288 g) as an oil.

Workup

  1. customremained below -55° C
  2. customThe reaction was quenched with water
  3. additiondiluted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried (anhyd Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-d597635f5e74409381529529a70cec48
Source dataset
uspto-grants-1998_11
Patent number
US05837704

Reaction notes

Loading…