反応 #50468

反応方程式

methyl iodide

5-chloroindanone

dimethylcarbonate

NaH

→

title compound

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

溶媒

THF

反応条件

後処理

1. 1
   温度the mixture was heated
2. 2
   温度to reflux under N2 overnight
3. 3
   温度to reflux overnight
4. 4
   温度The reaction was then cooled
5. 5
   その他partitioned between ether and 5% aqueous NaHCO3
6. 6
   洗浄the aqueous extracts were washed twice with ether
7. 7
   乾燥The combined aqueous extracts were dried over MgSO4
8. 8
   濃縮concentrated to 11.24 g of a brown oil

実験手順

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).

出典