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To a flame dried round bottom flask 0.5 g (3.6 mmol) of l-(2-hydroxyethyl)-lW- pyrrole-2,5-dione and 0.7 g (4.0 mmol) of methanesulfonic anhydride was added. The flask was evacuated and refilled with nitrogen. The flask was heated to 105C and stirred for 3.5 hr. The reaction was cooled to room temperature and dissolved in ethyl acetate (5 mL). The solution was taken up into a separatory funnel and washed four times with a saturated solution of sodium carbonate (40 mL). The aqueous layers were collected and washed with ethyl acetate (50 mL). The organic layers were combined and dried with MgS04 and concentrated in vacuo. The product was recrystallized from t-butyl methyl ether to yield 43 % (0.347 g, 1.58 mmol) of 2-(2,5-dioxo-2,5-dihydro-lH-pyrrol- l-yl)ethyl methanesulfonate.XH NMR (400 MHz, CD3CI) 6.78 (s, 2H), 4.41 (t, J = 5.23, 2H), 3.90 (t, J = 5.23, 2H), 3.04 (s, 3H)
Maleic anhydride 0.6mmol weighed into three neck round bottom flask, dissolve with 5ml of acetone, 0.66mmol ethanolamine with 5ml of acetone was dissolved by constant pressure funnel was slowly added dropwise three-necked flask, with magnetic stirring. After the reaction at room temperature for 1h , the acetone solvent was removed by rotary evaporation, use 5ml of toluene as a solvent, 0.012g of anhydrous sodium acetate were added to the reaction system, 0.2ml of triethylamine, 0.018 g of hydroquinone, 115 deg.] C was slowly warmed to reflux for 2.5h, tracing the reaction by thin layer chromatography on silica plates.After the reaction was cooled to room temperature, the solvent was removed by rotary evaporation, to obtain a concentrate, the concentrate was subjected to silica gel column chromatography (eluent: VPetroleum ether: VEthyl acetate= 12: 1), and collecting the target fluid, the rotation solvent in vacuo to give the desired product.Yield 30percent.
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