Aluminium lithium hydride → (3,5-Dimethylpyridin-4-yl)methanol

HRID 577237Notes

Reaction equation

HRID 577237 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([CH3:19])[C:13]=1[C:14](OCC)=[O:15]>C1COCC1>[CH3:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([CH3:19])[C:13]=1[CH2:14][OH:15]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59589494Ethyl 3,5-dimethylisonicotinate

Product 1

HCID 22663284(3,5-Dimethylpyridin-4-yl)methanolYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 0° C. mixture of lithium aluminum hydride (2.0 g, 53 mmol) in anhydrous THF (100 mL) was slowly added a solution of ethyl 3,5-dimethylpyridine-4-carboxylate (4.77 g, 26.6 mmol) in anhydrous THF (30 mL). The reaction mixture was stirred at 0° C. for 1.5 hours. The reaction was quenched with 5 N NaOH. Water (100 mL) and EtOAc (100 mL) were added. The mixture was stirred for 30 minutes. The solid material was removed by filtration. The organic layer was recovered. The aqueous layer was extracted with EtOAc (2×50 mL). The combined organic extracts were dried over MgSO4, filtered, evaporated, and dried in vacuo, affording (3,5-dimethylpyridin-4-yl)methanol (2.55 g, 70% yield). The product was used without further purification.

Workup

  1. customThe reaction was quenched with 5 N NaOH
  2. additionWater (100 mL) and EtOAc (100 mL) were added
  3. stirringThe mixture was stirred for 30 minutes
  4. customThe solid material was removed by filtration
  5. customThe organic layer was recovered
  6. extractionThe aqueous layer was extracted with EtOAc (2×50 mL)
  7. dry with materialThe combined organic extracts were dried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customdried in vacuo

Sources & evidence

ORD record
ord-fc42d655202640b19789a21ecc56acd0
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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