Sodium borohydride → HCID 86723690, compound

HRID 577458Notes

Reaction equation

HRID 577458 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH:15]=[O:16])=[C:13]([CH2:17][CH3:18])[CH:12]=[C:11]([CH3:19])[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]([CH2:17][CH3:18])[CH:12]=[C:11]([CH3:19])[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86723691HCID 86723691, compound

Product 1

HCID 86723690HCID 86723690, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 0° C. solution of 2-(benzyloxy)-4-ethyl-6-methylpyridine-3-carbaldehyde (Cpd CC, 323 mg, 1.28 mmol) in methanol (4.27 mL) was added sodium borohydride (54 mg, 1.41 mmol). After 1 hour, the reaction mixture was concentrated under vacuum then diluted with ethyl acetate (20 mL) and water (10 mL). The organic layer was washed with brine (5 mL), then dried over sodium sulfate, filtered, and concentrated under vacuum. The residue was purified by column chromatography (heptane/EtOAc) to give [2-(benzyloxy)-4-ethyl-6-methylpyridin-3-yl]methanol (Cpd DD, 280 mg, 85% yield) as a colorless oil.

Workup

  1. concentrationthe reaction mixture was concentrated under vacuum
  2. additionthen diluted with ethyl acetate (20 mL) and water (10 mL)
  3. washThe organic layer was washed with brine (5 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by column chromatography (heptane/EtOAc)

Sources & evidence

ORD record
ord-caba9073e3d34811ace72d2f276fce38
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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