Tributylstannane → (E)-triethoxy(2-(tributylstannyl)vinyl)silane

HRID 244305

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].[CH2:14]([O:16][Si:17]([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])[C:18]#[CH:19])[CH3:15]>CC(N=NC(C#N)(C)C)(C#N)C>[CH2:21]([O:20][Si:17]([O:23][CH2:24][CH3:25])([O:16][CH2:14][CH3:15])/[CH:18]=[CH:19]/[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])[CH3:22]

Participants

Conditions

Temperature: 80 °C

Procedure

Tributyltin hydride (1.9 mL, 7.2 mmol, 1.0 equiv) and triethoxy(ethynyl)silane (1.5 g, 7.9 mmol, 1.1 equiv) were combined. AIBN (60 mg, 0.36 mmol, 0.05 equiv) was added and the resulting yellow solution was heated to 80° C. Upon reaching 80° C., the reaction exothermed to 104° C. The yellow solution was cooled back to 80° C. and stirred for 20 h. The reaction mixture was cooled to provide the title compound as a pale yellow oil (3.5 g, 99% crude yield): IR (thin film) 2957 (s), 2925 (s), 2873 (m), 2854 (m) cm−1; 1H NMR (400 MHz, CDCl3) δ 7.43 (d, J=24 Hz, 1H), 6.37 (d, J=24 Hz, 1H), 3.83 (q, J=7 Hz, 6H), 1.49 (m, 6H), 1.29 (m, 6H), 1.22 (t, J=7 Hz, 9 H), 0.82-0.92 (m, 15 H).

Workup

customUpon reaching 80° C.
customthe reaction exothermed to 104° C
temperatureThe yellow solution was cooled back to 80° C.
temperatureThe reaction mixture was cooled

Sources & evidence

ORD record: ord-48b6901412864ccaa3a78bc1e1853cf1
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658568B2

Linked notes

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