Tributyltin Chloride → Trimethyl((tributylstannyl)ethynyl)silane
Reaction equation
[Li]CCCC.[C:6]([Si:8]([CH3:11])([CH3:10])[CH3:9])#[CH:7].[CH2:12]([Sn:16](Cl)([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][CH2:14][CH3:15]>C1COCC1>[CH3:9][Si:8]([CH3:11])([CH3:10])[C:6]#[C:7][Sn:16]([CH2:17][CH2:18][CH2:19][CH3:20])([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:12][CH2:13][CH2:14][CH3:15]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
n-BuLi (1.6 M, 24.4 mL, 39 mmol) was added dropwise to a solution of ethynyltrimethylsilane (4.0 g, 41 mmol) in THF (40 mL) at −78° C. and gradually warmed to 0° C. over 30 min. The reaction mixture was cooled to −78° C. again and tributyltin chloride (11.4 mL, 39 mmol) in THF (30 mL) was added dropwise to the resultant mixture. The reaction mixture was stirred for 18 h at room temperature and quenched with water (20 mL). The mixture was extracted with diethyl ether (2×100 mL) and the combined organic extracts were washed with brine (50 mL). The organic phase was dried and concentrated to give yellow oil (15.0 g, 95%), which was used directly in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ 1.67-1.45 (m, 6H), 1.45-1.20 (m, 6H), 0.98 (t, 6H, J=8.4 Hz), 0.90 (t, 9H, J=7.2 Hz), 0.16 (s, 9H).
Workup
- temperatureThe reaction mixture was cooled to −78° C. again
- customquenched with water (20 mL)
- extractionThe mixture was extracted with diethyl ether (2×100 mL)
- washthe combined organic extracts were washed with brine (50 mL)
- customThe organic phase was dried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-b987481b2fa945d693c7a4929a1e0fb3
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09231215B2
Reaction notes
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