Ethyl 2-methyl-3-(4-methylphenyl)-2-pyridin-3-ylpropanoate → 2-Methyl-3-(4-methylphenyl)-2-pyridin-3-ylpropan-1-ol

HRID 1860666Notes

Reaction equation

HRID 1860666 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][C:12]([C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)[C:13](OCC)=[O:14]>C1COCC1.C(OCC)(=O)C>[CH3:11][C:12]([C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)[CH2:13][OH:14]

Participants

5

Reactant 2

HCID 18624198Ethyl 2-methyl-3-(4-methylphenyl)-2-pyridin-3-ylpropanoateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 186242042-Methyl-3-(4-methylphenyl)-2-pyridin-3-ylpropan-1-ol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of diisobutylaluminum hydride 120 ml. 120 mmol, 1.0M in THF) was added to a solution of the product of STEP 2 (11.6 g, 38.7 mmol) in 100 ml THF at 0° C. over 20 min. After 1 h, the reaction was diluted with 25 ml ethyl acetate and quenched with 75 ml H2O. The resulting mixture was filtered through a short column of Celite®, and washed with ethyl acetate. Filtrate was extracted with ethyl acetate (3×100 ml). The combined organic layer was washed with brine, dried with MgSO4, and concentrated. The residue was purified by chromatography (on silica gel, ethyl acetate) to give a pale brown liquid in 4.1 g. NMR spectra of the product were consistent for the proposed structure.

Workup

  1. customquenched with 75 ml H2O
  2. filtrationThe resulting mixture was filtered through a short column of Celite®
  3. washwashed with ethyl acetate
  4. extractionFiltrate was extracted with ethyl acetate (3×100 ml)
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography (on silica gel, ethyl acetate)
  9. customto give a pale brown liquid in 4.1 g

Sources & evidence

ORD record
ord-b65386796ef9425c92b085bf030af490
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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