Trimethyltin chloride → 2-Propyl-5-trimethylstannylthiophene
Reaction equation
[CH2:1]([C:4]1[S:5][CH:6]=[CH:7][CH:8]=1)[CH2:2][CH3:3].[Li]CCCC.[CH3:14][Sn:15](Cl)([CH3:17])[CH3:16]>C1COCC1>[CH2:1]([C:4]1[S:5][C:6]([Sn:15]([CH3:17])([CH3:16])[CH3:14])=[CH:7][CH:8]=1)[CH2:2][CH3:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2-propylthiophene (5.0 g, 39.6 mmol) was dissolved in 160 ml THF and n-BuLi (27 ml, 1.6 M in hexanes, 43.6 mmol) was added dropwise at 0° C. The mixture was stirred at 0° C. for 1 h and then cooled down to −78° C. A solution of trimethyltin chloride (8.679 g, 43.6 mmol) in 50 ml THF was added dropwise. The mixture was allowed to warm slowly to room temperature and stirred for 2 h. After quenching with ice water and aqueous work-up, the product was obtained as a light brown liquid (10.1348 g, 88.6% yield).
Workup
- temperaturecooled down to −78° C
- temperatureto warm slowly to room temperature
- stirringstirred for 2 h
- customAfter quenching with ice water and aqueous work-up
Sources & evidence
- ORD record
- ord-1d04b97f23154b188e90e1085d10f754
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367717B2
Reaction notes
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