Reaction #213920

ord-ed3f9eaae94f4193abd114e291ec9a02

Reaction equation

C#CCC(CCCC)(O[Si](C)(C)C)C(OC)OC
4-dimethoxymethyl-4-trimethylsiloxy-1-octyne
CCC[CH2][SnH]([CH2]CCC)[CH2]CCC
tri-n-butylstannyl hydride
CC(C)(C#N)N=NC(C)(C)C#N
azobisisobutyronitrile
→
CCCCC(C/C=[CH]/[Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC)(O[Si](C)(C)C)C(OC)OC
title compound
CCCCC(C/C=[CH]/[Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC)(O[Si](C)(C)C)C(OC)OC
E-1-tri-n-Butylstannyl-4-dimethoxymethyl-4-trimethylsiloxy-1-octene

Reactants

C#CCC(CCCC)(O[Si](C)(C)C)C(OC)OC
4-dimethoxymethyl-4-trimethylsiloxy-1-octyne
CCC[CH2][SnH]([CH2]CCC)[CH2]CCC
tri-n-butylstannyl hydride
CC(C)(C#N)N=NC(C)(C)C#N
azobisisobutyronitrile

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONA mixture of 10.0 g
  2. 2
    workup.DISTILLATIONThe excess hydride is distilled off
  3. 3
    workup.DISTILLATIONthe residue is purified by molecular distillation (bath temperature=170°-175° C., 0.2mm.)
  4. 4
    Otherto give 20.5 g

Procedure

A mixture of 10.0 g. (36.7 mmoles) of 4-dimethoxymethyl-4-trimethylsiloxy-1-octyne, 12.82 g. (44 mmoles) of tri-n-butylstannyl hydride 100 mg. of azobisisobutyronitrile is heated to 140° C. under argon for 2 hours. The excess hydride is distilled off and the residue is purified by molecular distillation (bath temperature=170°-175° C., 0.2mm.) to give 20.5 g. of the title compound.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04254036uspto-grants-1981_03