반응 #50468

반응 방정식

methyl iodide

5-chloroindanone

dimethylcarbonate

NaH

→

title compound

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

용매

THF

반응 조건

후처리

1. 1
   온도the mixture was heated
2. 2
   온도to reflux under N2 overnight
3. 3
   온도to reflux overnight
4. 4
   온도The reaction was then cooled
5. 5
   기타partitioned between ether and 5% aqueous NaHCO3
6. 6
   세척the aqueous extracts were washed twice with ether
7. 7
   건조The combined aqueous extracts were dried over MgSO4
8. 8
   농축concentrated to 11.24 g of a brown oil

실험 절차

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).

출처