Tributylstannane → HCID 85444619, compound

HRID 848886Notes

Reaction equation

HRID 848886 reaction equation
[CH2:1]=[C:2]([CH2:15][CH2:16][CH3:17])[CH:3]([O:7][Si:8]([CH2:13][CH3:14])([CH2:11][CH3:12])[CH2:9][CH3:10])[CH2:4][C:5]#[CH:6].[CH2:18]([SnH:22]([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH3:21]>>[CH2:1]=[C:2]([CH2:15][CH2:16][CH3:17])[CH:3]([O:7][Si:8]([CH2:13][CH3:14])([CH2:11][CH3:12])[CH2:9][CH3:10])[CH2:4][CH:5]=[CH:6][Sn:22]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:18][CH2:19][CH2:20][CH3:21]

Participants

3

Reactant 2

HCID 5948TributylstannaneHCID 12786182HCID 12786182, compound

Product 1

HCID 85444619HCID 85444619, compound

Conditions

Temperature
150 °C

Procedure

A mixture of 20 g. of 5-methylene-4-triethylsilyloxy-1-octyne, 25.36 g. of tri-n-butylstannane and 0.1 g. of azobisisobutyrylnitrile is placed in an oil bath at 100° C. After 10 minutes an exotherm raises the temperature to 150° C. The mixture is then heated at 130°-140° C. for 1.5 hours. The excess tri-n-butylstannane is distilled off at 130° C. (1 mm.) and the residue is distilled in a Kugelrohr at 120°-140° C., 0.15-0.05 mm., giving the product as a colorless liquid.

Workup

  1. additionA mixture of 20 g
  2. temperatureThe mixture is then heated at 130°-140° C. for 1.5 hours
  3. distillationThe excess tri-n-butylstannane is distilled off at 130° C. (1 mm.)
  4. distillationthe residue is distilled in a Kugelrohr at 120°-140° C.

Sources & evidence

ORD record
ord-78122dca335949188e12f1eeb4aff279
Source dataset
uspto-grants-1981_10
Patent number
US04297516

Reaction notes

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