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

HRID 645574Notes

Reaction equation

HRID 645574 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[N:13][C:12]=1[CH2:17][CH3:18])C>O1CCCC1>[CH2:17]([C:12]1[C:11]([CH2:10][OH:9])=[CH:16][CH:15]=[CH:14][N:13]=1)[CH3:18]

Participants

4

Reactant 2

HCID 14580149Ethyl 2-ethylnicotinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 19690951(2-Ethylpyridin-3-yl)methanolYield 69.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of LiAlH4 (0.83 g, 21.76 mmol) in tetrahydrofuran (50 ml) was added drop wise a solution of 2-ethyl-nicotinic acid ethyl ester (Breitmaier et al, Tetrahedron, 26, 1970, 5907-5910) (3 g, 16.74 mmol) in tetrahydrofuran (25 ml) at −50° C. After addition, the temperature was slowly allowed to increase to 0° C. After 3 h, the reaction was quenched with saturated NH4Cl, filtered and washed with 1M NaHCO3 (50 ml). The aqueous layer was extracted with ethyl acetate (3×50 ml). Combined organic extract were dried (Na2SO4), filtered and concentrated to yield 1.6 g (54%) of product as a yellowish liquid. MS (ESI+) m/z 138 (M+H)+;

Workup

  1. additionAfter addition
  2. customthe reaction was quenched with saturated NH4Cl
  3. filtrationfiltered
  4. washwashed with 1M NaHCO3 (50 ml)
  5. extractionThe aqueous layer was extracted with ethyl acetate (3×50 ml)
  6. extractionCombined organic extract
  7. dry with materialwere dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b3be5e73d03247ec90277355c9537889
Source dataset
uspto-grants-2010_04
Patent number
US07704997B1

Reaction notes

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