Reacción #1121761

Ecuación de reacción

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

Rendimiento 64.0%

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

Rendimiento 64.0%

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe precipitate was filtered off
2. 2
   LavadoThe filtrate was washed with 20 ml of diluted hydrochloride solution, water
3. 3
   Secadodried over anhydrous magnesium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Otroevaporated under vacuum
6. 6
   OtroThe residue was purified by flash chromatography on silica gel

Procedimiento

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).

Fuente