Oxazole → 2-(Triethylstannyl)oxazole

HRID 2220123Notes

Reaction equation

HRID 2220123 reaction equation
C([Li])CCC.[O:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[CH2:11]([Sn:13](Br)([CH2:16][CH3:17])[CH2:14][CH3:15])[CH3:12]>CCOCC>[CH2:11]([Sn:13]([CH2:16][CH3:17])([CH2:14][CH3:15])[C:7]1[O:6][CH:10]=[CH:9][N:8]=1)[CH3:12]

Participants

5

Reactant 3

HCID 9255OxazoleHCID 17701Triethyltin bromideHCID 178418339Butyllithium

Product 1

HCID 149317842-(Triethylstannyl)oxazole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyllithium (1.6M, 11 mL, 17.38 mmol) was added to a solution of oxazole (1.0 g, 14.48 mmol) in anhydrous ether (20 mL) stirred at −78° C. under nitrogen. After 5 min, triethylstannyl bromide (2.07 g, 7.24 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 the sub-title compound as a brown oily residue (1.0 g), which was used without further purification in the next step.

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

Sources & evidence

ORD record
ord-9bc0976528cf49e19bf1a5450fbb81da
Source dataset
uspto-grants-2008_08
Patent number
US07417050B2

Reaction notes

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