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

HRID 1441602Notes

Reaction equation

HRID 1441602 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-ac0560d7bebd4db6b59569558cfd408c
Source dataset
uspto-grants-2010_02
Patent number
US07655666B2

Reaction notes

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