Tributylstannane → (E)-trimethyl(2-(tributylstannyl)vinyl)silane
Reaction equation
[CH2:1]([SnH:5]([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[C:14]([Si:16]([CH3:19])([CH3:18])[CH3:17])#[CH:15]>CC(N=NC(C#N)(C)C)(C#N)C>[CH3:17][Si:16]([CH3:19])([CH3:18])/[CH:14]=[CH:15]/[Sn:5]([CH2:1][CH2:2][CH2:3][CH3:4])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:10][CH2:11][CH2:12][CH3:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
Tributyltin hydride (2.0 mL, 7.3 mmol, 1.0 equiv) and ethynyltrimethylsilane (2.1 mL, 15 mmol, 2.0 equiv) were combined, AIBN (60 mg, 0.36 mmol, 0.05 equiv) was added, and the resulting colorless neat solution was heated to 80° C. Upon heating, the reaction exothermed to −110° C. The reaction mixture was cooled back to 80° C. and stirred for 20 h. The reaction mixture was cooled to 23° C. to afford the crude title compound as a pale yellow oil (2.8 g, 99% crude yield): 1H NMR (400 MHz, CDCl3) δ 6.96 (d, J=22.5 Hz, 1H), 6.60 (d, J=22.5 Hz, 1H), 1.44-1.54 (m, 6H), 1.23-1.35 (m, 6H), 0.82-0.91 (m, 15H), 0.03 (s, 9H).
Workup
- temperatureUpon heating
- customthe reaction exothermed to −110° C
- temperatureThe reaction mixture was cooled back to 80° C.
- temperatureThe reaction mixture was cooled to 23° C.
Sources & evidence
- ORD record
- ord-2e11b529c474474284eecc861e5e5d70
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658568B2
Reaction notes
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