Reaction #50468

Reaction equation

methyl iodide

5-chloroindanone

dimethylcarbonate

NaH

→

title compound

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

Solvents

THF

Conditions

Workup

1. 1
   Temperaturethe mixture was heated
2. 2
   Temperatureto reflux under N2 overnight
3. 3
   Temperatureto reflux overnight
4. 4
   TemperatureThe reaction was then cooled
5. 5
   Otherpartitioned between ether and 5% aqueous NaHCO3
6. 6
   Washthe aqueous extracts were washed twice with ether
7. 7
   DryingThe combined aqueous extracts were dried over MgSO4
8. 8
   Concentrationconcentrated to 11.24 g of a brown oil

Procedure

To a mixture of 8.0 g of 5-chloroindanone and 4.2 ml of dimethylcarbonate in 60 ml of THF was added 4.0 g of 60% NaH and the mixture was heated to reflux under N2 overnight. After this time the reaction was cooled to room temperature and 4.0 ml of methyl iodide was added and the mixture was reheated to reflux overnight. The reaction was then cooled and partitioned between ether and 5% aqueous NaHCO3 and the aqueous extracts were washed twice with ether. The combined aqueous extracts were dried over MgSO4 and concentrated to 11.24 g of a brown oil. Chromatogrpahy on silica gel (10% ethyl acetate/hexane) afforded 4.25 g of the title compound as a brown oil. 1H NMR (CDCl3) δ 1.52 (s, 3H), 2.96 (d, 1H), 3.68 (s, 3H), 3.69 (d, 1H), 7.40 (d, 1H), 7.47 (s, 1H), 7.71 (d, 1H).

Source