Ethyl 2,4-dimethylnicotinate → 2,4-Dimethyl-3-pyridinemethanol

HRID 418997Notes

Reaction equation

HRID 418997 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[C:11]1[C:16]([CH3:17])=[CH:15][CH:14]=[N:13][C:12]=1[CH3:18])C>C1COCC1>[CH3:18][C:12]1[C:11]([CH2:10][OH:9])=[C:16]([CH3:17])[CH:15]=[CH:14][N:13]=1

Participants

4

Reactant 2

HCID 736245Ethyl 2,4-dimethylnicotinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 103293512,4-Dimethyl-3-pyridinemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium aluminum hydride in THF (1.0 M, 40 mL, 40 mmol) placed in a 100-mL round bottom flask equipped with a magnetic stirring bar was cooled in an ice bath and cautiously treated with a solution of 2,4-dimethyl-nicotinic acid ethyl ester (5.4 g, 30 mmol) in anhydrous THF (10 mL) over 5 min period. After the addition was complete the cold bath was removed and the mixture was allowed to stir at room temperature for 2 h. The reaction mixture was then cooled in an ice bath and the excess LAH was quenched by drop wise addition of water until gas evolution stopped. The reaction mixture was then basified with 2M NaOH to pH 9-10. Ether (100 mL) was added the mixture was washed with 1 M NaOH, water and brine. The organic layer was dried over MgSO4 and the solvent was evaporated to yield (2,4-dimethyl-pyridin-3-yl)-methanol as a white solid. MS: (M+H)/z=138.

Workup

  1. customequipped with a magnetic stirring bar
  2. temperaturewas cooled in an ice bath
  3. additionAfter the addition
  4. customwas removed
  5. temperatureThe reaction mixture was then cooled in an ice bath
  6. customthe excess LAH was quenched by drop wise addition of water until gas evolution
  7. additionEther (100 mL) was added the mixture
  8. washwas washed with 1 M NaOH, water and brine
  9. dry with materialThe organic layer was dried over MgSO4
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a82f9d4caa5849919d92c1cc23bb41a3
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

Loading…