Methanesulfonic Acid → 5-Methyl-3-oxo-1-phenylindene-2-carboxylic acid ethyl ester

HRID 19534Notes

Reaction equation

HRID 19534 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C:5]([C:13](=[O:21])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=1)=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].CS(O)(=O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([O:3][C:4]([C:5]1[C:13](=[O:21])[C:14]2[C:19](=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=2)[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:22])[CH3:2]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 686968932-(3-Methylbenzoyl)-3-phenyl acrylic acid ethyl ester

Product 1

HCID 686992925-Methyl-3-oxo-1-phenylindene-2-carboxylic acid ethyl esterYield 27.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(3-Methylbenzoyl)-3-phenyl acrylic acid ethyl ester (1 g, 3.39 mmol) obtained in Step 2 was dissolved in dichloromethane, and methanesulfonic acid (5.22 g, 54.35 mmol) was added thereto, followed by stirring for 3 hrs at RT. Once the reaction was completed, the mixture was cooled to 0° C., neutralized with sodium bicarbonate, and extracted with dichloromethane. The organic layer was separated, dried over anhydrous MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 273 mg of the titled compound (yield: 27%).

Workup

  1. temperaturethe mixture was cooled to 0° C.
  2. extractionextracted with dichloromethane
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated under a reduced pressure
  6. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-4bdb37fea78e49ed9039741b1fdd5db3
Source dataset
uspto-grants-2010_06
Patent number
US07745439B2

Reaction notes

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