Methanesulfonic Acid → 3-(3-Benzyl-3H-imidazol-4-yl)-5-methoxy-6,7-dimethylindan-1-one

HRID 1017746Notes

Reaction equation

HRID 1017746 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[CH2:11]([N:18]1[C:22]([CH:23]=[CH:24][C:25](O)=[O:26])=[CH:21][N:20]=[CH:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CS(O)(=O)=O.[OH-].[Na+]>O>[CH2:11]([N:18]1[C:22]([CH:23]2[C:5]3[C:6](=[C:7]([CH3:8])[C:2]([CH3:1])=[C:3]([O:9][CH3:10])[CH:4]=3)[C:25](=[O:26])[CH2:24]2)=[CH:21][N:20]=[CH:19]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 762692,3-DimethylanisoleHCID 537408633-(3-Benzyl-3h-imidazol-4-yl)-acrylic acid

Product 1

HCID 184052653-(3-Benzyl-3H-imidazol-4-yl)-5-methoxy-6,7-dimethylindan-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
92.5 °C

Procedure

A mixture of 2,3-dimethylanisole (2.0 g), 3-(3-benzyl-3H-imidazol-4-yl)-acrylic acid (3.4 g) and methanesulfonic acid (60 ml) is heated at 90-95° C. for 45 minutes.The cooled reaction mixture is poured into water and is made alkaline with sodium hydroxide solution. The product is extracted into ethyl acetate which is washed with water, dried with sodium sulfate and evaporated in reduced pressure. The crude product is purified by flash chromatography by eluting with methylene chloride-methanol solution. The yield is 1.1 g.

Workup

  1. customThe cooled reaction mixture
  2. extractionThe product is extracted into ethyl acetate which
  3. washis washed with water
  4. dry with materialdried with sodium sulfate
  5. customevaporated in reduced pressure
  6. customThe crude product is purified by flash chromatography
  7. washby eluting with methylene chloride-methanol solution

Sources & evidence

ORD record
ord-e34e6031fefc4ace83f6ad4169c2a52b
Source dataset
uspto-grants-2002_11
Patent number
US06479530B2

Reaction notes

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