Tributylstannane → 4-Cyclopropyl-4-trimethylsiloxy-1-(tri-n-butylstannyl)-trans-1-octene

HRID 1395299Notes

Reaction equation

HRID 1395299 reaction equation
[CH:1]1([C:4]([O:12][Si:13]([CH3:16])([CH3:15])[CH3:14])([CH2:8][CH2:9][CH2:10][CH3:11])[CH2:5][C:6]#[CH:7])[CH2:3][CH2:2]1.[CH2:17]([SnH:21]([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH3:20].N(C(C)(C)C#N)=NC(C)(C)C#N>>[CH:1]1([C:4]([O:12][Si:13]([CH3:16])([CH3:14])[CH3:15])([CH2:8][CH2:9][CH2:10][CH3:11])[CH2:5]/[CH:6]=[CH:7]/[Sn:21]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:17][CH2:18][CH2:19][CH3:20])[CH2:2][CH2:3]1

Participants

4

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 13078752[(4-Cyclopropyloct-1-yn-4-yl)oxy](trimethyl)silane

Product 1

HCID 128003054-Cyclopropyl-4-trimethylsiloxy-1-(tri-n-butylstannyl)-trans-1-octene

Conditions

Temperature
85 °C

Procedure

A stirred mixture of 23.8 g of 4-cyclopropyl-4-trimethylsiloxy-1-octyne (Example 10), 28 ml of tri-n-butyltin hydride, and 50 mg of azobisisobutyronitrile under nitrogen is heated to 85° C. After the resulting exothermic reaction subsides the mixture is heated at 130° C. for 1 hour. The crude product is evaporatively distilled to give a liquid, p.m.r. spectrum (CDCl3): δ 0.10 (trimethylsiloxy group), 2.33 (doublet, =CHCH2), and 6.02 (vinyl hydrogens).

Workup

  1. customAfter the resulting exothermic reaction
  2. temperatureis heated at 130° C. for 1 hour
  3. distillationThe crude product is evaporatively distilled
  4. customto give a liquid, p.m.r

Sources & evidence

ORD record
ord-80f7b26c1c9e494fa65b589352926af7
Source dataset
uspto-grants-1980_05
Patent number
US04202989

Reaction notes

Loading…