反应 #1121756

反应方程式

2-Hydroxycarbonylmethyl-4-tetrahydropyranyloxy-2-cyclopenten-1-one

2-naphthol

1,3-dicyclohexylcarbodiimide

→

title compound

2-(2-Naphthyloxycarbonylmethyl)-4-hydroxy-2-cyclopenten-1-one

溶剂

dichloromethane

dichloromethane

反应条件

后处理

1. 1
   过滤The precipitate was filtered off
2. 2
   洗涤The filtrate was washed with 20 ml of diluted hydrochloride solution, water
3. 3
   干燥dried over anhydrous magnesium sulfate
4. 4
   过滤filtered
5. 5
   其他evaporated under vacuum
6. 6
   workup.DISSOLUTIONThe crude product was dissolved in 30 ml acetone
7. 7
   workup.ADDITION6 ml water, further added with 0.3 g p-toluenesulfonic acid
8. 8
   workup.STIRRINGstirred overnight
9. 9
   其他Upon completion of the reaction, acetone
10. 10
    其他was evaporated
11. 11
    workup.ADDITIONthe reaction mixture was diluted with ethyl acetate
12. 12
    洗涤washed with an aqueous sodium bicarbonate solution
13. 13
    过滤dehydration, filtration, and evaporation, and purification by chromatography on silica gel

实验过程

5 g of 2-Hydroxycarbonylmethyl-4-tetrahydropyranyloxy-2-cyclopenten-1-one (21 mmol) obtained from Example 5, 2-naphthol (4.7 g, 32 mmol), dichloromethane (50 ml), and 0.2 g 4-(dimethylamine)pyridine were added together to a 50 ml dichloromethane solution containing 1,3-dicyclohexylcarbodiimide (7 g, 34 mmol). The reaction mixture was stirred at room temperature for about 4 hours. The precipitate was filtered off. The filtrate was washed with 20 ml of diluted hydrochloride solution, water, dried over anhydrous magnesium sulfate, filtered, and evaporated under vacuum. The crude product was dissolved in 30 ml acetone and 6 ml water, further added with 0.3 g p-toluenesulfonic acid and stirred overnight. Upon completion of the reaction, acetone was evaporated and the reaction mixture was diluted with ethyl acetate and washed with an aqueous sodium bicarbonate solution and a brine solution. The organic liquid was subjected to the previous work-up procedure, including dehydration, filtration, and evaporation, and purification by chromatography on silica gel to obtain the title compound as white solid. MP: 81° C. (4.2 g, 71%) 1H-NMR (CDCl3/TMS): δ 7.82 (m,2H), 7.78 (d, 1H), 7.55 (m,2H), 7.46 (m,2H), 7.21 (dd, 1H), 5.04 (m, 1H), 3.56 (s, 2H), 2.89 (dd, 1H), 2.38 (dd, 1H), 1.60 (brs, 1H).

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