Tributyltin Chloride → 1-benzyloxy-5-tributylstannanyl-1H-pyrazole

HRID 1894082Notes

Reaction equation

HRID 1894082 reaction equation
[CH2:1]([O:8][N:9]1[CH:13]=[CH:12][CH:11]=[N:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.[Sn:19](Cl)([CH2:28][CH2:29][CH2:30][CH3:31])([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH2:22][CH3:23]>C1COCC1>[CH2:1]([O:8][N:9]1[C:13]([Sn:19]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:20][CH2:21][CH2:22][CH3:23])=[CH:12][CH:11]=[N:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 100580151H-Pyrazole, 1-(phenylmethoxy)-HCID 178418339Butyllithium

Product 1

HCID 104795011-benzyloxy-5-tributylstannanyl-1H-pyrazoleYield 106%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-benzyloxy-1H-pyrazole (1.17 g, 6.72 mmol) in THF (15 mL) at −78° C. was added dropwise n-BuLi (4.6 mL, 1.6M, 7.4 mmol). The mixture was stirred at −78° C. for 2 h before addition of Bu3SnCl (1.99 mL, 7.38 mmol). The mixture was kept at this temperature for 1 h and was then allowed to warm up to r.t. and stirred for 1 h. The mixture was concentrated in vacuo and hexanes was added. The insoluble material was removed by filtration and the filtrate was concentrated in vacuo to afford 1-benzyloxy-5-tributylstannanyl-1H-pyrazole (3.3 g, 100%) as a yellow syrup.

Workup

  1. concentrationThe mixture was concentrated in vacuo and hexanes
  2. additionwas added
  3. customThe insoluble material was removed by filtration
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-37eaacc5984d45f6b99e07fbad34d3ae
Source dataset
uspto-grants-2013_08
Patent number
US08513268B2

Reaction notes

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