Sodium cyanoborohydride → (5-(Phenylethynyl)pyridin-3-yl)methanol

HRID 606917Notes

Reaction equation

HRID 606917 reaction equation
C([BH3-])#N.[Na+].[C:5]1([C:11]#[C:12][C:13]2[CH:14]=[C:15]([CH:19]=[O:20])[CH:16]=[N:17][CH:18]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(OCC)(=O)C>[C:5]1([C:11]#[C:12][C:13]2[CH:14]=[C:15]([CH2:19][OH:20])[CH:16]=[N:17][CH:18]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 10679834HCID 10679834, compound

Product 1

HCID 67047855(5-(Phenylethynyl)pyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Add sodium cyanoborohydride (0.31 g, 4.98 mmol) to a solution of 5-phenylethynyl-pyridine-3-carbaldehyde, (prepared as described in EXAMPLE 5), (0.86 g, 4.15 mmol) and stir at room temperature for 2 h. Dilute with ethyl acetate, wash with an aqueous saturated solution of bicarbonate, dry (magnesium sulfate), filter and concentrate. Purify by silica gel chromatography, eluting with 0:100 to 50:50 ethyl acetate:hexanes, to give the title compound as a colorless oil which solidifies on standing (0.465 g, 53%).

Workup

  1. washwash with an aqueous saturated solution of bicarbonate
  2. dry with materialdry (magnesium sulfate)
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify by silica gel chromatography
  6. washeluting with 0:100 to 50:50 ethyl acetate

Sources & evidence

ORD record
ord-049bb610b4b8404db10eb70123e6bf3f
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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