Ethyl 2-ethylnicotinate → (2-Ethylpyridin-3-yl)methanol

HRID 630213Notes

Reaction equation

HRID 630213 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:9]1[C:14]([C:15](OCC)=[O:16])=[CH:13][CH:12]=[CH:11][N:10]=1)[CH3:8]>C1COCC1>[CH2:7]([C:9]1[C:14]([CH2:15][OH:16])=[CH:13][CH:12]=[CH:11][N:10]=1)[CH3:8]

Participants

4

Reactant 2

HCID 14580149Ethyl 2-ethylnicotinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 19690951(2-Ethylpyridin-3-yl)methanolYield 84.3%

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 2-ethylpyridine-3-carboxylate (4.8 g, 26.8 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 (200 mL) and EtOAc (200 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 (2×100 mL). The combined organic extracts were dried over MgSO4, filtered, evaporated, and dried in vacuo, affording (2-ethylpyridin-3-yl)methanol (3.1 g, 84% yield), which was used without further purification.

Workup

  1. customThe reaction was quenched with 5 N NaOH
  2. additionWater (200 mL) and EtOAc (200 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 (2×100 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-911928f423544f029e3331f9bc870531
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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