تفاعل #50468

معادلة التفاعل

methyl iodide

5-chloroindanone

dimethylcarbonate

NaH

→

title compound

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

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe mixture was heated
2. 2
   درجة الحرارةto reflux under N2 overnight
3. 3
   درجة الحرارةto reflux overnight
4. 4
   درجة الحرارةThe reaction was then cooled
5. 5
   أخرىpartitioned between ether and 5% aqueous NaHCO3
6. 6
   غسيلthe aqueous extracts were washed twice with ether
7. 7
   تجفيفThe combined aqueous extracts were dried over MgSO4
8. 8
   تركيزconcentrated to 11.24 g of a brown oil

الإجراء التجريبي

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).

المصدر