Sodium borohydride → (4-Iodo-2-methoxy-pyridin-3-yl)methanol

HRID 2308358Notes

Reaction equation

HRID 2308358 reaction equation
[BH4-].[Na+].[CH:3]([C:5]1[C:6]([O:12][CH3:13])=[N:7][CH:8]=[CH:9][C:10]=1[I:11])=[O:4]>CO>[OH:4][CH2:3][C:5]1[C:6]([O:12][CH3:13])=[N:7][CH:8]=[CH:9][C:10]=1[I:11]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 100383814-Iodo-2-methoxynicotinaldehyde

Product 1

HCID 11437022(4-Iodo-2-methoxy-pyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Solid NaBH4 (28 mg, 0.74 mmol) was added in one portion to a solution of 3-formyl-4-iodo-2-methoxypyridine (prepared according to the method of Fang et al., J. Org. Chem., 1994, 59, 6142) (98 mg, 0.37 mmol) in methanol (4 mL) at −5° C. Vigorous bubbling was observed and the yellow reaction solution turned colorless. The reaction was immediately quenched by the addition of water (2 mL) and the methanol was removed under reduced pressure. The resulting residue was diluted with ethyl acetate (20 mL) and water (20 mL). The aqueous layer was separated and extracted with ethyl acetate (3×10 mL). The organic fractions were combined, dried (MgSO4), filtered and concentrated to give 3-(hydroxymethyl)-4-iodo-2-methoxypyridine as a colorless, crystalline solid. This material was used in the next reaction without further purification. R/0.4 (30% ethyl acetate/petrol elution). MS (APCI, m/z 266 (M++1, 100%). 1H NMR (200 MHz, CDCl3) δ 3.98 (s, 3H), 4.80 (s, 2H) 7.34 (d, J=4.0 Hz, 1H), 7.70 (d, J=4.0 Hz, 1H).

Workup

  1. customprepared
  2. customat −5° C
  3. customVigorous bubbling
  4. customThe reaction was immediately quenched by the addition of water (2 mL)
  5. customthe methanol was removed under reduced pressure
  6. additionThe resulting residue was diluted with ethyl acetate (20 mL) and water (20 mL)
  7. customThe aqueous layer was separated
  8. extractionextracted with ethyl acetate (3×10 mL)
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-b1ac2429aef34bc484b37bc4d04d4dc0
Source dataset
uspto-grants-2004_12
Patent number
US06835753B2

Reaction notes

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