Reaktion #50468

Reaktionsgleichung

methyl iodide

5-chloroindanone

dimethylcarbonate

NaH

→

title compound

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

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was heated
2. 2
   Temperaturto reflux under N2 overnight
3. 3
   Temperaturto reflux overnight
4. 4
   TemperaturThe reaction was then cooled
5. 5
   Sonstigepartitioned between ether and 5% aqueous NaHCO3
6. 6
   Waschenthe aqueous extracts were washed twice with ether
7. 7
   TrocknenThe combined aqueous extracts were dried over MgSO4
8. 8
   Einengenconcentrated to 11.24 g of a brown oil

Vorschrift

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).

Quelle