Potassium Carbonate → HCID 66728158, compound

HRID 1409528Notes

Reaction equation

HRID 1409528 reaction equation
[Br:1][C:2]1[C:3]([OH:8])=[N:4][CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:15]([O:17][CH2:18]Cl)[CH3:16]>CC(C)=O>[Br:1][C:2]1[C:3]([O:8][CH2:18][O:17][CH2:15][CH3:16])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Procedure

To a round-bottomed flask was added 3-bromo-2-hydroxypyridine (5 g, 28.7 mmol) and potassium carbonate (9.93 g, 71.8 mmol) in Acetone (300 mL). The suspension was stirred at ambient temperature for 30 min and then treated with the drop-wise addition of chloromethyl ethyl ether (2.78 mL, 30.6 mmol) via addition funnel. The mixture was stirred at ambient temperature overnight. The reaction mixture was filtered and the filtrate partitioned between EtOAc and water. The combined organic layers were washed with water, saturated solution of sodium bicarbonate and brine, dried over Mg2SO4, filtered and concentrated. The crude material was to afford 2.46 g of desired product as a clear oil which was used without further purification.

Workup

  1. stirringThe mixture was stirred at ambient temperature overnight
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate partitioned between EtOAc and water
  4. washThe combined organic layers were washed with water, saturated solution of sodium bicarbonate and brine
  5. dry with materialdried over Mg2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c40c5c1b705749a781cf6b3e25a51ead
Source dataset
uspto-grants-2014_12
Patent number
US08921363B2

Reaction notes

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