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

HRID 1898002Notes

Reaction equation

HRID 1898002 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-d06da5acd6cc452884e1f905f29c607b
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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