Potassium Carbonate → HCID 23291347, compound

HRID 1602906Notes

Reaction equation

HRID 1602906 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 mirxture 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-2bea5efdb84242e8a3ed28c8890f5347
Source dataset
uspto-grants-1999_11
Patent number
US05985886

Reaction notes

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