Tributyltin Chloride → 1-Isopropyl-5-tributylstannanyl-1H-pyrazole
Reaction equation
[Li+].CC([N-]C(C)C)C.[CH:9]([N:12]1[CH:16]=[CH:15][CH:14]=[N:13]1)([CH3:11])[CH3:10].[CH2:17]([Sn:21](Cl)([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH3:20]>C1COCC1>[CH:9]([N:12]1[C:16]([Sn:21]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:17][CH2:18][CH2:19][CH3:20])=[CH:15][CH:14]=[N:13]1)([CH3:11])[CH3:10]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a cold (−78° C.) solution of LDA (prepared from n-BuLi (7.99 mL, 1.6 M, 1.1 eq) and diisopropylamine (1.82 mL, 1.1 eq)) in THF, a solution of 1-isopropyl-1H-pyrazole (1.28 g, 11.6 mmol) in THF was added dropwise while keeping the temperature below −70° C. At the end of the addition, the mixture was stirred at −78° C. for 30 min. Tributyltin chloride (3.44 mL, 1.1 eq) was then added dropwise while keeping the temperature below −70° C. At the end of the addition, the mixture was stirred for 1 h at −78° C. and for 2 h at r.t. The solvent was removed in vacuo and the crude oil was dissolved into AcOEt. The organic phase was washed with water and dried over Na2SO4. The solution was concentrated in vacuo to afford a yellow oil (3.82 g, 82%).
Workup
- customthe temperature below −70° C
- additionAt the end of the addition
- customthe temperature below −70° C
- additionAt the end of the addition
- stirringthe mixture was stirred for 1 h at −78° C. and for 2 h at r.t
- customThe solvent was removed in vacuo
- dissolutionthe crude oil was dissolved into AcOEt
- washThe organic phase was washed with water
- dry with materialdried over Na2SO4
- concentrationThe solution was concentrated in vacuo
Sources & evidence
- ORD record
- ord-aca4ecfb40e944a2a97662f6637b5dd3
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07655666B2
Reaction notes
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