Hydrogen iodide → Ethyl 6-hydroxymethyl-4-iodopyridine-2-carboxylate

HRID 1513993Notes

Reaction equation

HRID 1513993 reaction equation
[I:1][C:2]1[CH:7]=[C:6]([C:8](OCC)=[O:9])[N:5]=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:3]=1.[BH4-].[Na+].I.C([O-])(O)=O.[Na+]>CCO>[OH:9][CH2:8][C:6]1[N:5]=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:3]=[C:2]([I:1])[CH:7]=1

Participants

6

Reactant 4

HCID 24841Hydrogen iodideHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 14145737Diethyl 4-iodopyridine-2,6-dicarboxylate

Product 1

HCID 68482661Ethyl 6-hydroxymethyl-4-iodopyridine-2-carboxylateYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 1 (5.24 g, 15.0 mmol) was dissolved in EtOH (270 ml) at 40° C. NaBH4 (0.57 g, 15 0 mmol) was carefully added and the mixture stirred for 40 min. The reaction was stopped by adjusting the pH to 3 with 28% (w/w) aqueous hydriodic acid. The mixture was neutralized with saturated NaHCO3 solution and evaporated to dryness. The residue was suspended in water (150 mL) and the product was extracted from the aqueous phase with 10% EtOH/CH2Cl2 solution (3×150 ml). The combined organic fractions were dried with Na2SO4 and evaporated to dryness. Purification on silica gel (petroleum ether, by 40-60° C./ethyl acetate 2:5) yielded 2.89 g (63%) of the title compound.

Workup

  1. customevaporated to dryness
  2. extractionthe product was extracted from the aqueous phase with 10% EtOH/CH2Cl2 solution (3×150 ml)
  3. dry with materialThe combined organic fractions were dried with Na2SO4
  4. customevaporated to dryness
  5. customPurification on silica gel (petroleum ether, by 40-60° C./ethyl acetate 2:5)

Sources & evidence

ORD record
ord-e87d09f4956c43b587139796dbca47e5
Source dataset
uspto-grants-2012_07
Patent number
US08221719B2

Reaction notes

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