Tributylstannane → HCID 20442051, compound

HRID 1632702Notes

Reaction equation

HRID 1632702 reaction equation
[CH3:1][C:2]([O:11][Si:12]([CH3:15])([CH3:14])[CH3:13])([CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3][C:4]#[CH:5].N(C(C)(C)C#N)=NC(C)(C)C#N.[CH2:28]([SnH:32]([CH2:37][CH2:38][CH2:39][CH3:40])[CH2:33][CH2:34][CH2:35][CH3:36])[CH2:29][CH2:30][CH3:31]>>[CH3:1][C:2]([O:11][Si:12]([CH3:13])([CH3:14])[CH3:15])([CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3]/[CH:4]=[CH:5]/[Sn:32]([CH2:33][CH2:34][CH2:35][CH3:36])([CH2:37][CH2:38][CH2:39][CH3:40])[CH2:28][CH2:29][CH2:30][CH3:31]

Participants

4

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 20288815HCID 20288815, compound

Product 1

HCID 20442051HCID 20442051, compound

Conditions

Temperature
120 °C

Procedure

To a stirred mixture of 33.96 g of 4-methyl-4-trimethylsilyloxy nonyne and 150 mg of azobisisobutyronitrile at ambient temperature under argon was added 41 ml of tri-n-butyltin hydride via syringe. The mixture was slowly heated in an oil bath, with a rapid exothermic reaction to 120° C. taking place as the temperature reached 60° C. Heating to 130°-135° C. continued for one hour. The product was then allowed to cool and was then distilled to provide 74.5 g of (E)-4-methyl-4-trimethylsilyloxy-1-tri-n-butylstannyl-1-nonene (b.p. 162°-164° C. at 0.15-0.30 mm).

Workup

  1. customreached 60° C
  2. temperatureHeating to 130°-135° C.
  3. temperatureto cool
  4. distillationwas then distilled

Sources & evidence

ORD record
ord-04c9ee348ab44248aa0aed9f2f49e976
Source dataset
uspto-grants-1984_10
Patent number
US04477388

Reaction notes

Loading…