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

HRID 1592419노트

반응식

HRID 1592419 반응식
[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

참가 물질

6

반응물 4

HCID 241Benzene2회HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 450917322-(2-Methylpyridin-3-yl)propan-2-ol

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-bfc70b1d4ee64e9bbf1c03e1717c6429
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07291631B2

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