Tributyltin Chloride → 2-((Tert-butyldimethylsilyloxy)methyl)-5-(tributylstannyl)thiazole
Reaction equation
[Si:1]([O:8][CH2:9][C:10]1[S:11][CH:12]=[CH:13][N:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Li]C(C)(C)C.[Sn:20](Cl)([CH2:29][CH2:30][CH2:31][CH3:32])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH3:24].[NH4+].[Cl-]>C1COCC1>[Si:1]([O:8][CH2:9][C:10]1[S:11][C:12]([Sn:20]([CH2:25][CH2:26][CH2:27][CH3:28])([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:21][CH2:22][CH2:23][CH3:24])=[CH:13][N:14]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
2-((tert-butyldimethylsilyloxy)methyl)thiazole (8.0 g, 35 mmol) was dissolved in dry THF (350 mL) and the solution was cooled to −78° C. To this solution, t-BuLi (1.7 M, 25 mL, 42 mmol) was added dropwise. The reaction was warmed to −40° C. and stirred for 2 hours. Then, Bu3SnCl (14.6 g, 45 mmol) was added and the resulting mixture was allowed to warm to room temperature slowly and stirred for another 30 min. NH4Cl (aq.) was added to quench the reaction and extracted with EtOAc. The organics was dried and concentrated. The residue was purified with column (silica gel, 0˜30 EtOAc/hexane) to give the product 2-((tert-butyldimethylsilyloxy)methyl)-5-(tributylstannyl)thiazole (14.1 g)
Workup
- temperatureThe reaction was warmed to −40° C.
- temperatureto warm to room temperature slowly
- stirringstirred for another 30 min
- customto quench
- customthe reaction
- extractionextracted with EtOAc
- customThe organics was dried
- concentrationconcentrated
- customThe residue was purified with column (silica gel, 0˜30 EtOAc/hexane)
Sources & evidence
- ORD record
- ord-481e3b87cacc44ddbbcc93050697583b
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09227971B2
Reaction notes
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