Trimethyltin chloride → (4-Dodecyl-2-thienyl)trimethylstannane
Reaction equation
[CH2:1]([C:13]1[CH:17]=[CH:16][S:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[Li+].CC([N-]C(C)C)C.[CH3:26][Sn:27](Cl)([CH3:29])[CH3:28]>C1COCC1>[CH3:26][Sn:27]([CH3:29])([CH3:28])[C:16]1[S:15][CH:14]=[C:13]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH:17]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a stirred degassed homogeneous solution of 3-dodecyl thiophene (19) (2 g, 7.92 mmol) in THF at −78° C. was added LDA (4.75 ml, 9.51 mmol) drop wise. The mixture was stirred at −78° C. for 1 h, then trimethylstannylchloride dissolved in 9.5 ml of THF was added, and the solution warmed to room temperature. Stirring was continued for 2 h at room temperature. The mixture was washed with saturated NaHCO3 and extracted with diethylether. The organic layer was separated and dried over anhydrous sodium sulphate and concentrated under reduced pressure to give desired product 20 in 90% yield. 1H-NMR (CD2Cl2, 400 MHz) δ 7.19 (s, 1H), 7.02 (s, 1H), 2.63 (t, 2H), 1.62 (m. 2H), 1.2-1.4 (m, 18H), 0.88 (t, 3H), 0.34 (s, 9H).
Workup
- additionwas added
- temperaturethe solution warmed to room temperature
- stirringStirring
- waitwas continued for 2 h at room temperature
- washThe mixture was washed with saturated NaHCO3
- extractionextracted with diethylether
- customThe organic layer was separated
- dry with materialdried over anhydrous sodium sulphate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-3048503f6e7d49eaa15d7e919d2a3b20
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09221944B2
Reaction notes
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