Sodium Hydroxide → (4-Methylpyridin-2-yl)methanol

HRID 640106Notes

Reaction equation

HRID 640106 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([CH2:10][O:11]C(=O)C)[CH:5]=1>CO>[CH3:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([CH2:10][OH:11])[CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19912996(4-Methylpyridin-2-yl)methyl acetate

Product 1

HCID 12325388(4-Methylpyridin-2-yl)methanolYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

5 N Aqueous sodium hydroxide solution (2 mL) and methanol (4 mL) were added to acetic acid 4-methyl-pyridin-2-ylmethyl ester (774 mg, 4.69 mmol) described in Manufacturing Example 11-1-2, and this mixture was stirred for 10 minutes at 60° C. The reaction solution was partitioned into water and ethyl acetate. The separated aqueous layer was further extracted with ethyl acetate twice. The ethyl acetate layers were combined and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure to obtain the title compound (410 mg, 71.0%).

Workup

  1. customThe reaction solution was partitioned into water and ethyl acetate
  2. extractionThe separated aqueous layer was further extracted with ethyl acetate twice
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-e61005d79132460c98e8c9acbc85565f
Source dataset
uspto-grants-2010_04
Patent number
US07691882B2

Reaction notes

Loading…