Sodium borohydride → 6-Butoxy-2-hydroxymethylpyridine

HRID 912699Notes

Reaction equation

HRID 912699 reaction equation
[CH2:1]([O:5][C:6]1[N:11]=[C:10]([C:12](OC)=[O:13])[CH:9]=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[BH4-].[Na+]>C(O)C>[CH2:1]([O:5][C:6]1[N:11]=[C:10]([CH2:12][OH:13])[CH:9]=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydride3×HCID 67415067Methyl 6-butoxypyridine-2-carboxylate

Product 1

HCID 197561166-Butoxy-2-hydroxymethylpyridineYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 6-butoxypyridine-2-carboxylate (2.46 g, 11.8 mmol, obtained from Example 17(b)) was dissolved in absolute ethanol (112 mL) and sodium borohydride (1.78 g, 47.0 mmol, 4 equiv.) was added. After refluxing for 1 h, another 2 equivalents of sodium borohydride were added and then after 2 h more an additional 2 equivalents more sodium borohydride were added. After another 3 h the reaction was cooled to r.t. and concentrated in vacuo. The residue was partitioned between water and ethyl acetate. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo producing 1.92 g (91% yield, 10.7 mmol) of the title compound as a clear liquid.

Workup

  1. temperatureAfter refluxing for 1 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between water and ethyl acetate
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-521de58ff919405e8aedb28e2ae56921
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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