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

HRID 1987722Notes

Reaction equation

HRID 1987722 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. customVigorous bubbling
  3. customThe reaction was immediately quenched by the addition of water (2 mL)
  4. customthe methanol was removed under reduced pressure
  5. additionThe resulting residue was diluted with ethyl acetate (20 mL) and water (20 mL)
  6. customThe aqueous layer was separated
  7. extractionextracted with ethyl acetate (3×10 mL)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-bf139a28ad9446b2b7db92d9c954734b
Source dataset
uspto-grants-2009_06
Patent number
US07553809B2

Reaction notes

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