Water → 5-Chloro-2-methyl-3-pyridinemethanol

HRID 2071029Notes

Reaction equation

HRID 2071029 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7](OC)=[O:8].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:11]=[C:6]([CH2:7][OH:8])[C:5]([CH3:12])=[N:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 10867045Methyl 5-chloro-2-methylnicotinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 669614925-Chloro-2-methyl-3-pyridinemethanolYield 50%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

To a stirring solution of 950 mg (5.12 mmol) of methyl 5-chloro-2-methylnicotinate in 20 mL of THF at 0° C. was added 500 mg (13.2 mmol) of LiAlH4 in 2 portions. After stirring at 0° C. for about 1 h., the following were added in succession: 0.5 mL of H2O, 0.5 mL of 15% NaOH (aqueous), and 1.5 mL of brine. The ice bath was removed and stirring was continued for 2 h. The mixture was filtered through Celite and concentrated. Purification by flash silica gel chromatography (2% MeOH/CHCl3) provided 399 mg of (5-chloro-2-methylpyridin-3-yl)methanol as an orange-yellow oil in 50% yield.

Workup

  1. additionthe following were added in succession
  2. customThe ice bath was removed
  3. stirringstirring
  4. waitwas continued for 2 h
  5. filtrationThe mixture was filtered through Celite
  6. concentrationconcentrated
  7. customPurification by flash silica gel chromatography (2% MeOH/CHCl3)

Sources & evidence

ORD record
ord-4d7278b5523043d8b44c7062e6ef959d
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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