Methyl iodide → methyl 5-chloro-2,3-dihydro-2-mehtyl-1-oxo-1H-indene-2-carboxylate

HRID 2399775

Reaction equation

HRID 2399775 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[C:12](=O)([O:15]C)[O:13][CH3:14].[H-].[Na+].[CH3:20]I>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[C:6]([CH3:20])([C:12]([O:13][CH3:14])=[O:15])[CH2:5]2

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 1425995-Chloro-1-indanone

Product 1

HCID 19384693methyl 5-chloro-2,3-dihydro-2-mehtyl-1-oxo-1H-indene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-chloroindanone (10 g) and dimethyl carbonate (6.0 ml) in THF (80 ml) was added a 60% oil dispersion (5.0 g) of sodium hydride at room temperature, followed by heating at reflux for 12 hours. After cooling to room temperature, methyl iodide (5.0 ml) was added thereto, and the mixture was heated again at reflux for 12 hours. The reaction mixture was poured into ice-water and extracted with dichloromethane (300 ml×3). The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to chromatography on silica gel to give methyl 5-chloro-2,3-dihydro-2-mehtyl-1-oxo-1H-indene-2-carboxylate (yield, 5.3 g).

Workup

  1. temperatureby heating
  2. temperatureat reflux for 12 hours
  3. temperaturethe mixture was heated again
  4. temperatureat reflux for 12 hours
  5. extractionextracted with dichloromethane (300 ml×3)
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4e6f8a3052034b5c93c5d14b1b1f8695
Source dataset
uspto-grants-1995_09
Patent number
US05451607

Linked notes

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