A versatile preparation of 2-methyleneoxetanes

Journal of Organic Chemistry

Volumn 61, Issue 21, 1996, Pages 7248-7249

  Dollinger, Lisa M ^a   Howell, Amy R ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OXETANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029856072     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9611733     Document Type: Article

References (26)

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17. 2 in the dark. The reaction was monitored by TLC, and after the disappearance of the starting material (2-15 h) the solution was cooled and concentrated to half of its original volume. An equal volume of petroleum ether was then added, at which point a yellow precipitate formed. The mixture was passed through Celite with petroleum ether until the filtrate was colorless. After concentration, if large amounts of solid were present, the mixture was diluted with petroleum ether and filtered through Celite again. The residue was then purified by flash chromatography on silica gel (petroleum ether/ ethyl acetate/triethylamine 98.5:0.5:1).
18. All new compounds are fully characterized, and the requisite data can be found in the supporting information.
19. Concerned about the stability of both β-lactones and 2-methyleneoxetanes at elevated temperatures, in separate experiments we heated 7c and 10c at 70°C in toluene for 24 h. The lactone appeared to be unchanged; on the other hand, the oxetane showed significant decomposition.
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23. Compound 11a was prepared from 10i by the method used in the synthesis of 11b cited in ref 26. Experimental and spectral details can be found in the supporting information.
24. Zhi, J.; Melia, A. T.; Guerciolini, R.; Chung, J.; Kinberg, J.; Hauptman, J. B.; Patel, I. H. Clin. Pharm. Ther. 1994, 56, 82-85.
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