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ChemicalBook CAS DataBase List 1-ethenyl-2-oxabicyclo[2.2.2]octane-4-carboxylic acid
340023-04-3

1-ethenyl-2-oxabicyclo[2.2.2]octane-4-carboxylic acid synthesis

8synthesis methods
-

Yield:-

Steps:

Multi-step reaction with 7 steps
1: pyridine / 20 °C
2: hydrogenchloride / tetrahydrofuran / 5 h / Reflux
3: tetrahydrofuran / 5.25 h / -78 °C
4: sodium hydride / 1,2-dimethoxyethane; mineral oil / 2.5 h / Reflux
5: N,N-dimethyl-formamide / 100 °C
6: potassium carbonate / methanol; water / 2 h / 20 °C / Cooling
7: pyridinium dichromate / N,N-dimethyl-formamide / 3.5 h / 25 - 40 °C

References:

Singh, Sheo B.;Kaelin, David E.;Wu, Jin;Miesel, Lynn;Tan, Christopher M.;Meinke, Peter T.;Olsen, David;Lagrutta, Armando;Bradley, Prudence;Lu, Jun;Patel, Sangita;Rickert, Keith W.;Smith, Robert F.;Soisson, Stephen;Wei, Changqing;Fukuda, Hideyuki;Kishii, Ryuta;Takei, Masaya;Fukuda, Yasumichi [ACS Medicinal Chemistry Letters,2014,vol. 5,# 5,p. 609 - 614]