Réaction #1121761

Équation de réaction

2-hydroxycarbonylmethyl-4(R)-tetrahydropyranyloxy-2-cyclopenten-1-one

(R)-2-Hydroxycarbonylmethyl-4-tetrahydropyranyloxy-2-cyclopenten-1-one

2-naphthol

1,3-dicyclohexylcarbodiimide

→

titled compound

Rendement 64.0%

(R)-2-(2-Naphthoxycarbonylmethyl)-4-tetrahydropyranyloxy-2-cyclopenten-1-one

Rendement 64.0%

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
   AutreThe residue was purified by flash chromatography on silica gel

Mode opératoire

5 g of 2-hydroxycarbonylmethyl-4(R)-tetrahydropyranyloxy-2-cyclopenten-1-one (21 mmol) obtained from Example 44, 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 residue was purified by flash chromatography on silica gel to give the titled compound as white solid (3.8g, 64%). MP: 75° C.; [α]D+29.3° (c 1.0, CH3CN); 1H-NMR (CDCl3/TMS): δ 7.10˜7.90 (m, 8H), 4.72˜5.11 (m, 2H), 3.90 (m, 1H), 3.60 (m, 3H), 2.89 (m, 1H), 2.35˜2.60 (m, 1H), 1.40˜1.92 (m, 6H).

Source