Tributylstannane → E-1-Tri-n-butylstannyl-4-methyl-4-trimethylsilyloxy-1,7-octadiene

HRID 848918Notes

Reaction equation

HRID 848918 reaction equation
[CH3:1][C:2]([O:10][Si:11]([CH3:14])([CH3:13])[CH3:12])([CH2:6][CH2:7][CH:8]=[CH2:9])[CH2:3][C:4]#[CH:5].[CH2:15]([SnH:19]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH3:18].N(C(C)(C)C#N)=NC(C)(C)C#N>>[CH2:24]([Sn:19]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:20][CH2:21][CH2:22][CH3:23])/[CH:5]=[CH:4]/[CH2:3][C:2]([CH3:1])([O:10][Si:11]([CH3:13])([CH3:14])[CH3:12])[CH2:6][CH2:7][CH:8]=[CH2:9])[CH2:25][CH2:26][CH3:27]

Participants

4

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 12786233HCID 12786233, compound

Product 1

HCID 12786234E-1-Tri-n-butylstannyl-4-methyl-4-trimethylsilyloxy-1,7-octadiene

Conditions

Temperature
140 °C

Procedure

A mixture of 30 g. of 4-methyl-4-trimethylsilyloxy-oct-1-yn-7-ene, 58.66 g. of tri-n-butylstannane and 200 mg. of azobisisobutyronitrile is placed in a bath at 95° C. and stirred under argon. The mixture is heated at 140° C. for one hour and then at 140° C. under vacuum for 1.5 hours. The mixture is distilled via a Kugelrohr at 140° C., 0.06 mm. to give the product as a colorless liquid.

Workup

  1. additionA mixture of 30 g
  2. distillationThe mixture is distilled via a Kugelrohr at 140° C.

Sources & evidence

ORD record
ord-1c60a87ed36545fdbaa3e81d3f6747a2
Source dataset
uspto-grants-1981_10
Patent number
US04297516

Reaction notes

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