Ethyl 2-(propan-2-yl)pyridine-3-carboxylate → (2-Isopropylpyridin-3-yl)methanol

HRID 1688Notes

Reaction equation

HRID 1688 reaction equation
[CH:1]([C:4]1[C:9]([C:10](OCC)=[O:11])=[CH:8][CH:7]=[CH:6][N:5]=1)([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH:1]([C:4]1[C:9]([CH2:10][OH:11])=[CH:8][CH:7]=[CH:6][N:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 19690961Ethyl 2-(propan-2-yl)pyridine-3-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 19691012(2-Isopropylpyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 2-isopropyl-3-carboethoxypyridine (400 mg, 2 mmol) in distilled THF (50 mL) under nitrogen was cooled to 0° C. and lithium aluminum hydride (1M in THF) (2.07 mL) was added dropwise. The reaction was stirred for 18 hours at room temperature then cooled to 0° C. and quenched with EtOAc (100 μL), then H2O (100 μL), then 15% NaOH (100 μL), followed by H2O (300 μL). The mixture was filtered and the solvent was removed under reduced pressure. Toluene was added and the solvent was removed under reduced pressure to give the desired 2-isopropyl-3-hydroxymethylpyridine.

Workup

  1. temperaturethen cooled to 0° C.
  2. customquenched with EtOAc (100 μL)
  3. filtrationThe mixture was filtered
  4. customthe solvent was removed under reduced pressure
  5. additionToluene was added
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-13eeac45e3ff4344b45ee3f41e200838
Source dataset
uspto-grants-1998_03
Patent number
US05726172

Reaction notes

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