Water → 2-(Trimethylstannyl)furan

HRID 1722756Notes

Reaction equation

HRID 1722756 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.C([Li])CCC.[CH3:11][Sn:12](Cl)([CH3:14])[CH3:13].O>CCOCC>[CH3:11][Sn:12]([CH3:14])([CH3:13])[C:2]1[O:1][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8029FuranHCID 14016Trimethyltin chlorideHCID 178418339Butyllithium

Product 1

HCID 98133762-(Trimethylstannyl)furanYield 96.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-30 °C

Procedure

To a solution of 6.8 g furan in 100 ml dry ether at 0° C. under nitrogen was added 10.5 ml 9.5M n-butyllithium. The reaction mixture was heated at reflux for 15 min., then cooled to -30° C. and 19.9 g trimethyltin chloride was added. The reaction mixture was allowed to warm to room temperature and then poured into water. The ether layer was separated, washed with water and passed through an alumina column, eluting with hexane. Removal of the solvent provided 22.2 g (96%) 2-(trimethylstannyl)furan as a pale-yellow liquid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 15 min.
  3. temperatureto warm to room temperature
  4. customThe ether layer was separated
  5. washwashed with water
  6. washeluting with hexane
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-aa2fe65b8d0549c1bb485d131c39a3f1
Source dataset
uspto-grants-1989_08
Patent number
US04857539

Reaction notes

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