Sodium borohydride → HCID 17974485, compound

HRID 2252332Notes

Reaction equation

HRID 2252332 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[CH:11]=[O:12])=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[CH2:11][OH:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 17974502HCID 17974502, compound

Product 1

HCID 17974485HCID 17974485, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(6-chloro-pyridin-3-yloxy)-benzaldehyde (250 mg, 1.07 mmol) in methanol at ambient temperature was added sodium borohydride (49 mg, 1.3 mmol). The resulting reaction was stirred for 30 minutes, then quenched with saturated NaHCO3. The methanol was removed in vacuo, and the residue was diluted with water and extracted with ethyl acetate. The combined organics were washed with brine, dried over sodium sulfate, and concentrated in vacuo to an oil. The crude was purified by flash chromatography (eluting with 25% ethyl acetate/hexane) to give the above named compound as an oil (250 mg, 100%).

Workup

  1. customThe resulting reaction
  2. customquenched with saturated NaHCO3
  3. customThe methanol was removed in vacuo
  4. additionthe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. washThe combined organics were washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo to an oil
  9. customThe crude was purified by flash chromatography (eluting with 25% ethyl acetate/hexane)
  10. customto give the

Sources & evidence

ORD record
ord-85b4990ce9ea4d12a384763b2043b836
Source dataset
uspto-grants-2008_01
Patent number
US07321040B2

Reaction notes

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