Reaktion #73454

Reaktionsgleichung

4,10-dioxa-tricyclo[5.2.1.02,6]decane-3,5-dione

benzyl alcohol

→

10

7-oxa-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid monobenzyl ester

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturCooled to room temperature
2. 2
   Sonstigeevaporated
3. 3
   Sonstigeto remove solvent
4. 4
   SonstigeResidue obtained
5. 5
   Sonstigewas triturated with diisopropyl ether (20 mL)

Vorschrift

A mixture of 4,10-dioxa-tricyclo[5.2.1.02,6]decane-3,5-dione (8, 3.7 g, 22.0 mmol) and benzyl alcohol (9) (4.5 mL, 44.0 mmol) in dioxane was heated at 80° C. for 16 h. Cooled to room temperature and evaporated to remove solvent. Residue obtained was triturated with diisopropyl ether (20 mL) to give white solid of 10 which was filtered, washed with diisopropyl ether (10 mL) and dried. Yield: 3.6 g (59%). 1H NMR (300 MHz, CDCl3) δ 1.45-1.55 (m, 2H); 1.78-1.81 (m, 2H); 3.05 (s, 2H); 4.91 (d, J=9.4 Hz, 2H); 5.02 (d, J=6.3 Hz, 1H); 5.13 (d, J=6.3 Hz, 1H); 7.28-7.40 (m, 5H).

Quelle