Water → (2-Methoxypyridin-4-yl)methanol

HRID 1497328Notes

Reaction equation

HRID 1497328 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][N:11]=1)[C:6](O)=[O:7].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][OH:7])[CH:9]=[CH:10][N:11]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 8199422-Methoxyisonicotinic AcidHCID 21226445Aluminium lithium hydride

Product 1

HCID 14462410(2-Methoxypyridin-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of 2-methoxyisonicotinic acid (M1) (490 mg, 3.20 mmol) in anhydrous THF (15 ml) was added dropwise LAH (3.20 ml, 6.40 mmol) (2.0 N in Et2O), and the mixture was stirred at room temperature for overnight. The reaction mixture was cooled back to 0° C. and 0.28 ml H2O, 0.21 ml of 20% NaOH solution, 0.98 ml H2O were added drop-wise sequentially and stirred for 1 h. The solid was filtered and washed with THF and the filtrate was concentrated to give (2-methoxypyridin-4-yl)methanol (M2) as a clear oil that gave a mass ion (ES+) of 140.1 for M+H+.

Workup

  1. temperatureThe reaction mixture was cooled back to 0° C.
  2. stirringstirred for 1 h
  3. filtrationThe solid was filtered
  4. washwashed with THF
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-58938dd47e63450ba1cce9b04873e3b3
Source dataset
uspto-grants-2015_12
Patent number
US09199939B2

Reaction notes

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