Benzoxazole → 2-Triethylstannylbenzoxazole

HRID 2220124Notes

Reaction equation

HRID 2220124 reaction equation
C([Li])CCC.[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[CH:7]1.[CH2:15]([Sn:17](Br)([CH2:20][CH3:21])[CH2:18][CH3:19])[CH3:16]>CCOCC>[CH2:15]([Sn:17]([CH2:20][CH3:21])([CH2:18][CH3:19])[C:7]1[O:6][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=1)[CH3:16]

Participants

5

Reactant 3

HCID 9228BenzoxazoleHCID 17701Triethyltin bromideHCID 178418339Butyllithium

Product 1

HCID 689786342-Triethylstannylbenzoxazole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyllithium (1.6M, 6.0 mL, 9.57 mmol) was added to a solution of benzoxazole (950 mg, 7.98 mmol) in anhydrous ether (20 mL) stirred at −78° C. under nitrogen. After 10 min, triethylstannyl bromide (2.28 g, 7.98 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 which was used directly without further purification for 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-a6ccd87adc674d4f91f8b3b25741e14f
Source dataset
uspto-grants-2008_08
Patent number
US07417050B2

Reaction notes

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