Diethyl Ether → [6-(Pyridin-2-yl)pyridin-3-yl]methanol

HRID 1418074Notes

Reaction equation

HRID 1418074 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13](O)=[O:14])=[CH:9][N:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.[OH-].[Na+]>C1COCC1.O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][N:8]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 192752(2,2'-Bipyridine)-5-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 10352407[6-(Pyridin-2-yl)pyridin-3-yl]methanol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(pyrid-2-yl)-5-pyridine carboxylic acid (0.320 g, 1.60 mmol) in THF (5 mL) at 0° C. is added 1.0M lithium aluminum hydride in diethyl ether (1.60 mL, 1.60 mmol) over 10 minutes. The reaction is allowed to stir at ambient temperature for 3 hours, cooled to 0° C., and water (0.10 mL), 4N aq. NaOH (0.10 mL), and water (0.30 mL) are added sequentially. The reaction is filtered through a pad of Celite and the filtrate is evaporated in vacuo. The residue is purified by chromatography to afford the title compound.

Workup

  1. temperaturecooled to 0° C.
  2. filtrationThe reaction is filtered through a pad of Celite
  3. customthe filtrate is evaporated in vacuo
  4. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-9fd06ca1bc24439abd8e10bb709aa2dd
Source dataset
uspto-grants-1999_03
Patent number
US05880140

Reaction notes

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