Sodium borohydride → [2-(Benzyloxy)-4,6-dimethylpyridin-3-yl]methanol

HRID 577454Notes

Reaction equation

HRID 577454 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH:15]=[O:16])=[C:13]([CH3:17])[CH:12]=[C:11]([CH3:18])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([O:8][C:9]1[C:14]([CH2:15][OH:16])=[C:13]([CH3:17])[CH:12]=[C:11]([CH3:18])[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 229349822-(Benzyloxy)-4,6-dimethylnicotinaldehyde

Product 1

HCID 61255489[2-(Benzyloxy)-4,6-dimethylpyridin-3-yl]methanolYield 121.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

35 g×2 batches: To a 0° C. solution of 2-(benzyloxy)-4,6-dimethylpyridine-3-carbaldehyde (Cpd X, 35.0 g, 145 mmol) in CH3OH (1000 mL) was added NaBH4 (6.60 g, 174 mmol) in portions. The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under vacuum and the residue was diluted with NaHCO3 (sat., aq.). After the bubbling had stopped, the aqueous solution was extracted with EtOAc (2×500 mL). The combined organic layers were dried over Na2SO4, concentrated under vacuum, and purified by column chromatography (petroleum ether/EtOAc) to give [2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methanol (Cpd Y, 43 g, 61%) as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. additionthe residue was diluted with NaHCO3 (sat., aq.)
  3. extractionthe aqueous solution was extracted with EtOAc (2×500 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. custompurified by column chromatography (petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-31a7618495464330aa67de72eee55378
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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