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

HRID 1592419Notes

Reaction equation

HRID 1592419 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-bfc70b1d4ee64e9bbf1c03e1717c6429
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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