Tributylstannane → HCID 20442060, compound

HRID 1632701Notes

Reaction equation

HRID 1632701 reaction equation
[CH2:1]([Si:3]([CH2:15][CH3:16])([CH2:13][CH3:14])[O:4][C:5]([CH3:12])([CH2:9][CH2:10][CH3:11])[CH2:6][C:7]#[CH:8])[CH3:2].N(C(C)(C)C#N)=NC(C)(C)C#N.[CH2:29]([SnH:33]([CH2:38][CH2:39][CH2:40][CH3:41])[CH2:34][CH2:35][CH2:36][CH3:37])[CH2:30][CH2:31][CH3:32]>>[CH2:15]([Si:3]([CH2:13][CH3:14])([CH2:1][CH3:2])[O:4][C:5]([CH3:12])([CH2:9][CH2:10][CH3:11])[CH2:6]/[CH:7]=[CH:8]/[Sn:33]([CH2:34][CH2:35][CH2:36][CH3:37])([CH2:38][CH2:39][CH2:40][CH3:41])[CH2:29][CH2:30][CH2:31][CH3:32])[CH3:16]

Participants

4

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 20442050HCID 20442050, compound

Product 1

HCID 20442060HCID 20442060, compound

Procedure

A solution of 40.0 g of 4-triethylsilyloxy-4-methyl-1-heptyne, 180 mg of azobisisobutyronitrile, and 50 ml of tri-n-butyltin hydride is stirred under an argon atmosphere at 130° C. for 2 hours, then allowed to cool to ambient temperature. The excess tin hydride is removed by distillation and the residue purified to provide 63.5 g of the (E)-4-triethylsilyloxy-4-methyl-1-tri-n-butylstannyl-1-heptene (b.p. 160°-88° C. at 0.6 mm).

Workup

  1. customThe excess tin hydride is removed by distillation
  2. customthe residue purified

Sources & evidence

ORD record
ord-409ce8b6821d4587808b156fbe0b7af3
Source dataset
uspto-grants-1984_10
Patent number
US04477388

Reaction notes

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