Tributyltin Chloride → Carbamic acid, [2-(tributylstannyl)phenyl]-, 1,1-dimethylethyl ester
Reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:7])([CH3:4])([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].C([O-])(O)=O.[Na+]>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[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])([CH3:4])([CH3:2])[CH3:3]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
To a solution of N-(t-butoxycarbonyl)aniline (2.0 g, 10.35 mmol) in dry THF (50 mL) at 78° C., a solution of t-BuLi (2.7M in pentane, 26 mL, 25.88 mmol) was added dropwise over 30 min. The resulting yellow solution was warmed to −20° C. and stirred at this temperature for 2.5 h. n-Bu3SnCl (4.2 mL, 15.52 mmol) in dry THF (10 mL) was added over 20 min, and the solution stirred at −20° C. for 2 h, then at room temperature for 12 h. The reaction mixture was poured into NaHCO3 solution and extracted with ether. The extract was washed with water, brine, and dried over MgSO4. The solvent was evaporated and the resulting oil purified by flash chromatography in hexanes/ether (20: 1) to give 2-tributylstannylphenylcarbamic acid t-butyl ester (2.42 g, 54%).
Workup
- additionwas added over 20 min
- waitat room temperature for 12 h
- extractionextracted with ether
- washThe extract was washed with water, brine
- dry with materialdried over MgSO4
- customThe solvent was evaporated
- customthe resulting oil purified by flash chromatography in hexanes/ether (20: 1)
Sources & evidence
- ORD record
- ord-5c6a5099dc5d4fc2b5656b6cdd1adffa
- Source dataset
- uspto-grants-2003_01
- Patent number
- US06506769B2
Reaction notes
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