Tributylstannane → (E)-1-tri-n-butylstannyl-3-triethylsilyloxy-1-octene

HRID 224553Notes

Reaction equation

[CH2:1]([Si:3]([CH2:15][CH3:16])([CH2:13][CH3:14])[O:4][CH:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:6]#[CH:7])[CH3:2].N(C(C)(C)C#N)=NC(C)(C)C#N.[CH2:29]([SnH:33]([CH2:38][CH2:39][CH2:40][CH3:41])[CH2:34][CH2:35][CH2:36][CH3:37])[CH2:30][CH2:31][CH3:32]>>[CH2:38]([Sn:33]([CH2:29][CH2:30][CH2:31][CH3:32])([CH2:34][CH2:35][CH2:36][CH3:37])/[CH:7]=[CH:6]/[CH:5]([O:4][Si:3]([CH2:13][CH3:14])([CH2:1][CH3:2])[CH2:15][CH3:16])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:39][CH2:40][CH3:41]

Participants

Reactant 3

HCID 5948Tributylstannane

HCID 6547Azobisisobutyronitrile

HCID 126753463-Triethylsilyloxy-1-octyne

Product 1

HCID 20442056(E)-1-tri-n-butylstannyl-3-triethylsilyloxy-1-octene

Procedure

A solution of 20 g of 3-triethylsilyloxy-1-octyne, 150 mg of azobisisobutyronitrile, and 30 ml of tri-n-butyltin hydride is magnetically stirred under an argon atmosphere at 140° C. for 2 hours, (EXOTHERMIC), then cooled to ambient temperature. The excess tin hydride is removed by distillation (~70°/1.0 mm). The residue is purified by distillation to provide 36.5 g of the oil (bp 165° C. at 0.05 mm).

Workup

customThe excess tin hydride is removed by distillation (~70°/1.0 mm)
distillationThe residue is purified by distillation

Sources & evidence

ORD record: ord-08dd5583ae51474eba63d145237eb6e5
Source dataset: uspto-grants-1980_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04233231

Reaction notes

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