Isobutyraldehyde → 1-(3-Benzylquinolin-2-yl)-2-methylpropan-1-ol

HRID 271823Notes

Reaction equation

HRID 271823 reaction equation
[CH2:1]([C:8]1[C:9](I)=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Mg]Cl)(C)C.[CH:24](=[O:28])[CH:25]([CH3:27])[CH3:26].C(OCC)(=O)C>O1CCCC1>[CH2:1]([C:8]1[C:9]([CH:24]([OH:28])[CH:25]([CH3:27])[CH3:26])=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6561IsobutyraldehydeHCID 8857Ethyl AcetateHCID 598361933-Benzyl-2-iodoquinolineHCID 178418918HCID 178418918, compound

Product 1

HCID 598361951-(3-Benzylquinolin-2-yl)-2-methylpropan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-benzyl-2-iodoquinoline 11 (1 eq., 1.45 g) in dry tetrahydrofuran (20 ml) at −78° C., was added isopropyl magnesium chloride (3 eq., 6.3 ml). The color of the solution was changed from green to orange in 1 h. Isobutyraldehyde 12 (3 eq., 1.15 ml) was added and the reaction mixture was allowed to warm up to room temperature and stirred for another hour. Ethyl acetate was added. The organic layer was washed with saturated sodium bicarbonate, saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated. The crude material was purified by flash chromatography to yield 150 mg of 1-(3-benzylquinolin-2-yl)-2-methylpropan-1-ol 13.

Workup

  1. customorange in 1 h
  2. washThe organic layer was washed with saturated sodium bicarbonate, saturated sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-a0f4a983369d4ce6834f40fc75d858d0
Source dataset
uspto-grants-2008_11
Patent number
US07452996B2

Reaction notes

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