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

HRID 1891545Notes

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

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

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

Sources & evidence

ORD record: ord-c56210850a834a1da1fd726532421a29
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507530B2

Reaction notes

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