Réaction #1121755

Équation de réaction

2-ethoxycarbonylmethyl-4-hydroxy-2-cyclopenten-1-one

3,4-dihydro-2H-pyran

→

2-ethoxycarbonylmethyl-4-tetrahydropyranyloxy-2-cyclopenten-1-one

Rendement 95.1%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   AutreUpon completion of the reaction
2. 2
   Lavagethe reaction mixture was washed with 400 ml of a saturated aqueous sodium bicarbonate solution
3. 3
   Séchagedried over anhydrous magnesium sulfate
4. 4
   Concentrationconcentrated

Mode opératoire

100 g of 2-ethoxycarbonylmethyl-4-hydroxy-2-cyclopenten-1-one was dissolved in 1000 ml dichloromethane, and added with 55 g of 3,4-dihydro-2H-pyran and 2 g of p-toluenesulfonic acid monohydrate, and then stirred at room temperature for about 3 hours. Upon completion of the reaction, the reaction mixture was washed with 400 ml of a saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and concentrated to obtain 2-ethoxycarbonylmethyl-4-tetrahydropyranyloxy-2-cyclopenten-1-one (138.5 g). 1H-NMR (CDCl3/TMS): δ 7.40-7.68 (m, 1H), 4.70˜5.02 (m, 2H), 4.15 (q, 2H), 3.88 (m, 1H), 3.54 (m,1H), 3.23 (q, 2H), 2.79 (m,1H), 2.37 (m, 1H), 1.77 (m, 2H), 1.55 (m, 4H), 1.25 (t, 3H).

Source