Reaktion #1256506

Reaktionsgleichung

3-(4-phenylbenzyloxy)-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene

dimethyl carbonate

sodium methoxide

hydrochloric acid

→

methyl 3-(4-phenylbenzyloxy)-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene-6-carboxylate

Ausbeute 73.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux
2. 2
   Einengenwas concentrated under reduced pressure
3. 3
   Sonstigeto remove the organic solvent
4. 4
   Extraktionthe aqueous layer was extracted with a mixed solvent of ethyl acetate and THF ((30 ml/15 ml)×3)
5. 5
   TrocknenThe combined organic layers were dried with anhydrous magnesium sulfate
6. 6
   Einengenwere then concentrated under reduced pressure
7. 7
   EinengenThe objective fractions were concentrated under reduced pressure, diisopropyl ether
8. 8
   workup.ADDITIONwas added to the residue
9. 9
   Filtrationan insoluble material was collected by filtration
10. 10
    WaschenThe insoluble material was washed with diisopropyl ether
11. 11
    Sonstigewas then dried under reduced pressure

Vorschrift

To 3-(4-phenylbenzyloxy)-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene (2.90 g, 8.47 mmol) dissolved in dimethyl carbonate (80 ml) was added sodium methoxide (2.29 g, 42.4 mmol), and the resulting mixture was stirred at reflux with heating (110° C.) for 6 hours. The reaction mixture was mixed with 1 N hydrochloric acid (60 ml) under ice cooling and was concentrated under reduced pressure to remove the organic solvent, and then the aqueous layer was extracted with a mixed solvent of ethyl acetate and THF ((30 ml/15 ml)×3). The combined organic layers were dried with anhydrous magnesium sulfate and were then concentrated under reduced pressure, and the residue was subjected to column chromatography (silica gel: 50 g, ethyl acetate/hexane=1/30). The objective fractions were concentrated under reduced pressure, diisopropyl ether was added to the residue and an insoluble material was collected by filtration. The insoluble material was washed with diisopropyl ether and was then dried under reduced pressure to obtain methyl 3-(4-phenylbenzyloxy)-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene-6-carboxylate (2.47 g, 6.17 mmol, 73%).

Quelle