Reaktion #1121761

Reaktionsgleichung

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

Ausbeute 64.0%

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

Ausbeute 64.0%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe precipitate was filtered off
2. 2
   WaschenThe filtrate was washed with 20 ml of diluted hydrochloride solution, water
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated under vacuum
6. 6
   SonstigeThe residue was purified by flash chromatography on silica gel

Vorschrift

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).

Quelle