Tributyltin Chloride → 4-Tri-n-butylstannylfuran-2-carbonitrile

HRID 2220130Notes

Reaction equation

HRID 2220130 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[C:9]([C:12]#[N:13])[O:10][CH:11]=1.[CH2:14]([Sn:18](Cl)([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH3:17]>CCOCC>[CH2:23]([Sn:18]([CH2:14][CH2:15][CH2:16][CH3:17])([CH2:19][CH2:20][CH2:21][CH3:22])[C:7]1[CH:8]=[C:9]([C:12]#[N:13])[O:10][CH:11]=1)[CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 219862204-Bromofuran-2-carbonitrileHCID 178418339Butyllithium

Product 1

HCID 686152454-Tri-n-butylstannylfuran-2-carbonitrileYield 53%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyllithium (1.6M, 3.7 mL, 5.93 mmol) was added to a solution of 4-bromofuran-2-carbonitrile (850 mg, 4.94 mmol) in anhydrous ether (15 mL) stirred at −78° C. under nitrogen. After 10 min, tri-n-butylstannyl chloride (1.61 g, 4.94 mmol) was added, then the reaction mixture was allowed to warm to room temperature, and stirred for another 1 h. The mixture was quenched, and washed with 1N sodium hydroxide, dried through MgSO4, and then the solvent was evaporated to give a brown oily residue. Purification by flash chromatography using a gradient of ammoniated methanol in chloroform gave the sub-title compound as a yellow oil (1.0 g).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for another 1 h
  3. customThe mixture was quenched
  4. washwashed with 1N sodium hydroxide
  5. dry with materialdried through MgSO4
  6. customthe solvent was evaporated
  7. customto give a brown oily residue
  8. customPurification by flash chromatography

Sources & evidence

ORD record
ord-6310cf939366470baa4f36fbe280f5ee
Source dataset
uspto-grants-2008_08
Patent number
US07417049B2

Reaction notes

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