Water → HCID 61255848, compound

HRID 1747535Notes

Reaction equation

HRID 1747535 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[N:9]([C:13]2[CH:23]=[CH:22][C:16]([C:17](OCC)=[O:18])=[CH:15][N:14]=2)[CH:10]=[CH:11][N:12]=1.O.[OH-].[Na+]>C1COCC1>[CH3:7][C:8]1[N:9]([C:13]2[N:14]=[CH:15][C:16]([CH2:17][OH:18])=[CH:22][CH:23]=2)[CH:10]=[CH:11][N:12]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 55240554HCID 55240554, compound

Product 1

HCID 61255848HCID 61255848, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Lithium aluminum hydride (164 mg, 4.33 mmol) was suspended in THF (5 mL). A solution of ethyl 6-(2-methyl-1H-imidazol-1-yl)nicotinate (455 mg, 1.96 mmol) obtained in Step 1 in THF (5 mL) was added at 0° C. and the mixture was stirred at 0° C. for 30 minutes. To the reaction mixture were sequentially added water (0.146 mL), a 15% aqueous sodium hydroxide solution (0.146 mL), and water (0.492 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was filtered through Celite. The solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=97/3) to give (6-(2-methyl-1H-imidazol-1-yl)pyridin-3-yl)methanol (341 mg, 92% yield).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customThe solvent in the filtrate was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (chloroform/methanol=97/3)

Sources & evidence

ORD record
ord-c7656c734f0743d18b437d9dbffb2b40
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

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