Potassium Carbonate → HCID 15428581, compound

HRID 1585868Notes

Reaction equation

HRID 1585868 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.I[C:9]1[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=1.C([O-])([O-])=O.[K+].[K+]>[Cu]>[O:1]=[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]1[C:9]1[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 290124-Iodobenzyl alcoholHCID 178516071HCID 178516071, compound

Product 1

HCID 15428581HCID 15428581, compound

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

2-Hydroxypyridine (10.0 mmol; 956 mg), 4-iodobenzyl alcohol (17.09 mmol, 4.0 g), K2CO3 (11.0 mmol, 1.52 g), and copper (0.2 mmol, 15 mg) were mixed under argon and heated to 150° for 16 hours. The solid was partitioned between saturated NaHCO3 and EtOAc. The layers were separated and the aqueous layer was back extracted twice with EtOAc. The organic layers were combined, washed with brine, dried over MgSO4, filtered and concentrated to yield a yellow oil which was purified by flash chromatography (EtOAc) to give pure the title compound as a crystalline solid

Workup

  1. temperatureheated to 150° for 16 hours
  2. customThe solid was partitioned between saturated NaHCO3 and EtOAc
  3. customThe layers were separated
  4. extractionthe aqueous layer was back extracted twice with EtOAc
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto yield a yellow oil which
  10. customwas purified by flash chromatography (EtOAc)

Sources & evidence

ORD record
ord-a761eaa6fc454327ab2336ef92fe559b
Source dataset
uspto-grants-1999_08
Patent number
US05939439

Reaction notes

Loading…