Réaction #1121756

Équation de réaction

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

2-naphthol

1,3-dicyclohexylcarbodiimide

→

title compound

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

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   FiltrationThe precipitate was filtered off
2. 2
   LavageThe filtrate was washed with 20 ml of diluted hydrochloride solution, water
3. 3
   Séchagedried over anhydrous magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Autreevaporated 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
   AutreUpon completion of the reaction, acetone
10. 10
    Autrewas evaporated
11. 11
    workup.ADDITIONthe reaction mixture was diluted with ethyl acetate
12. 12
    Lavagewashed with an aqueous sodium bicarbonate solution
13. 13
    Filtrationdehydration, filtration, and evaporation, and purification by chromatography on silica gel

Mode opératoire

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).

Source