Tributyltin Chloride → Tributylstannane

HRID 893897Notes

Reaction equation

HRID 893897 reaction equation
[CH2:1]([Sn:5](Cl)([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].COCCO[AlH2-]OCCOC.[Na+].[H-].COCCO[Al+]OCCOC.[Na+].[H-]>C(OCC)C>[CH2:10]([SnH:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 16684438Red-AlHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 5948TributylstannaneYield 45.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Vit et al. in Eastman Organic Chemical Bulletin, 1974, vol. 46, No. 1, page 5 discloses a dehalogenation of tributyltin chloride with VITRIDE reducing agent (sodium bis (2-methoxyethoxy) aluminum hydride) in boiling diethyl ether. After a workup procedure including water quenching, ether extraction, drying, evaporation and distillation, substantially as shown by Van der Kerk supra, for the use of lithium aluminum hydride, 45.5% yield of tributyltin hydride is obtained. Although by this method tributyltin chloride is successfully reduced to the hydride, the yield is low and it calls for the use of diethyl ether which is notoriously volatile, flammable and explosive. The yield is so low as to render impractical, by this route, many interesting processes which involve the use of the expensive organotin halides.

Workup

  1. extractionwater quenching, ether extraction
  2. customdrying
  3. customevaporation and distillation

Sources & evidence

ORD record
ord-f94e4e3268994ca39d94ffa3ebebccf3
Source dataset
uspto-grants-1981_08
Patent number
US04282166

Reaction notes

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