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

HRID 1592419ノート

反応式

HRID 1592419 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-bfc70b1d4ee64e9bbf1c03e1717c6429
出典データセット
uspto-grants-2007_11
特許番号
US07291631B2

反応ノート

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