Dimethyl Carbonate → 1H-Indene-2-carboxylic acid, 5-chloro-2,3-dihydro-1-oxo-, methyl ester

HRID 1570

Reaction equation

HRID 1570 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7]2.[H][H].[CH3:16][O:17][C:18](=O)[O:19]C>C(COC)OC>[C:18]([CH:8]1[CH2:7][C:6]2[C:10](=[CH:11][CH:12]=[C:4]([Cl:3])[CH:5]=2)[C:9]1=[O:13])([O:17][CH3:16])=[O:19]

Participants

6

Reactant 4

HCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 1425995-Chloro-1-indanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 110423911H-Indene-2-carboxylic acid, 5-chloro-2,3-dihydro-1-oxo-, methyl esterYield 45%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
60 °C

Procedure

To a mixture of sodium hydride (2.4 g, 60% in mineral oil, 0.06 mole) and 50 ml dry dimethoxyethane, 5-chloroindanone (50 g, 0.03 mole) in 50 ml dimethoxyethane was added dropwise at room temperature. The mixture was stirred at room temperature until hydrogen evolution ceased. Then dimethylcarbonate (27 g, 0.3 mole) was added dropwise at room temperature and the reaction was heated to 60° C. for one hour. The reaction was cooled to room temperature, quenched with 100 ml H2O, acidified to pH 5 with concentrated HCl and extracted with ethyl ether (3×100 ml). The ether extract was washed with brine (100 ml), dried over anhydrous MgSO4 and stripped to yield 3.0 g (45%) of the desired product as a tan solid.

Workup

  1. additionwas added dropwise at room temperature
  2. temperatureThe reaction was cooled to room temperature
  3. customquenched with 100 ml H2O
  4. extractionextracted with ethyl ether (3×100 ml)
  5. extractionThe ether extract
  6. washwas washed with brine (100 ml)
  7. dry with materialdried over anhydrous MgSO4

Sources & evidence

ORD record
ord-38cbb1529cc84ed082175760bc576022
Source dataset
uspto-grants-1998_03
Patent number
US05726176

Linked notes

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