Potassium Carbonate → HCID 23291347, compound

HRID 1586037Notes

Reaction equation

HRID 1586037 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH2:20][OH:21])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[O:16][CH2:17][O:18][CH3:19].I[CH2:23][CH2:24][CH3:25].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[OH:21][CH2:20][C:6]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=2[O:16][CH2:17][O:18][CH3:19])=[C:2]([O:1][CH2:23][CH2:24][CH3:25])[CH:3]=[N:4][CH:5]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 23291356HCID 23291356, compound

Product 1

HCID 23291347HCID 23291347, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-hydroxy-5-hydroxymethyl-4-(2-methoxymethoxy-4-methoxy-phenyl)-pyridine (550 mg, 1.89 mmol), iodopropane (0.210 ml, 2.15 mmol), potassium carbonate (3 g) in dry DMF (70 ml) was stirred overnight at rt. The mixture was dissolved in water and extracted with a 1:1 hexane:t-butyl methyl ether solution (×3) and washed with brine, dried (Na2SO4), and concentrated to afford the title compound as a greenish oil. (527 mg, 84%)

Workup

  1. extractionextracted with a 1:1 hexane
  2. washt-butyl methyl ether solution (×3) and washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-734174380e8d46fea2dcf37bbfab738c
Source dataset
uspto-grants-1999_08
Patent number
US05942516

Reaction notes

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