Water → (6-Methylpyridin-3-yl)methanol

HRID 1295983Notes

Reaction equation

HRID 1295983 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](OC)=[O:7])=[CH:4][N:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1>[CH3:1][C:2]1[N:3]=[CH:4][C:5]([CH2:6][OH:7])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24083Sulfuric acid magnesium salt (1:1)HCID 231548Methyl 6-methylnicotinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 11228788(6-Methylpyridin-3-yl)methanolYield 82.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 6-methylnicotinate (50 g, 0.33 mol) in anhydrous tetrahydrofuran (100 ml) was slowly added dropwise to a suspension of LAH (12.6 g, 0.33 mol) in anhydrous tetrahydrofuran (500 ml) over a period of 30 minutes while cooling on ice, and the mixture was stirred at the same temperature for 1 hour and 20 minutes. After confirming completion of the reaction by thin layer chromatography, H2O (25 ml) was slowly added dropwise over a period of 30 minutes while cooling on ice, and the stirring was continued at room temperature for 30 minutes. Magnesium sulfate was added for drying, and the precipitate was filtered through celite and washed three times with ethyl acetate. The solvent was distilled off under reduced pressure to yield the title compound (33.6 g, 82%) as a yellow oil.

Workup

  1. temperaturewhile cooling on ice
  2. additionwas slowly added dropwise over a period of 30 minutes
  3. temperaturewhile cooling on ice
  4. waitthe stirring was continued at room temperature for 30 minutes
  5. customfor drying
  6. filtrationthe precipitate was filtered through celite
  7. washwashed three times with ethyl acetate
  8. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-db8ed84ebd4a4cccb791420fd577f7c0
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

Loading…