Benzene → 2-Methyl-3-(2-phenyl-2-propanyl)pyridine

HRID 250981Notes

Reaction equation

HRID 250981 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][C:6]1[C:11]([C:12](O)([CH3:14])[CH3:13])=[CH:10][CH:9]=[CH:8][N:7]=1.[OH-].[Na+].[CH:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCOC(C)=O>[CH3:5][C:6]1[C:11]([C:12]([CH3:14])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:13])=[CH:10][CH:9]=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 241Benzene2×HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 450917322-(2-Methylpyridin-3-yl)propan-2-ol

Product 1

HCID 450972722-Methyl-3-(2-phenyl-2-propanyl)pyridineYield 75%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of AlCl3 (2.173 g, 16.3 mmol) in benzene (20 mL) was added a solution of 2-(2-methyl-pyridin-3-yl)-propan-2-ol (0.455 g, 3.00 mmol) in benzene (10 mL) and the resultant mixture was stirred at room temperature overnight. The mixture was poured onto ice (˜200 mL), diluted with EtOAc (200 mL), and neutralized with 10 N NaOH (4 mL). The phases were separated and the organic phase was washed with brine (3×25 mL), dried (MgSO4), and concentrated. Purification of the crude material by column chromatography on silica gel (20:1 CH2Cl2-MeOH) provided 0.479 g (75%) of 2-methyl-3-(1-methyl-1-phenyl-ethyl)-pyridine as a colorless oil. 1H NMR (CDCl3) δ 1.68 (s, 6H), 2.01 (s, 3H), 7.11-7.20 (m, 4H), 7.24-7.30 (m, 2H), 7.86 (dd, 1H, J=8.1, 1.5 Hz), 8.39 (dd, 1H, J=4.8, 1.5 Hz).

Workup

  1. additionThe mixture was poured onto ice (˜200 mL)
  2. customThe phases were separated
  3. washthe organic phase was washed with brine (3×25 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customPurification of the crude material by column chromatography on silica gel (20:1 CH2Cl2-MeOH)

Sources & evidence

ORD record
ord-3955e9cc2cf541efb2d90e8ae7c2b527
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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