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Volumn 32, Issue 39, 1991, Pages 5295-5298

3-bromo-2-pyrone: an easily prepared chameleon diene and a synthetic equivalent of 2-pyrone in thermal diels-alder cycloadditions

(4) Posner, Gary H a Nelson, Todd D a Kinter, Chris M a Afarinkia, Kamyar a

a JOHNS HOPKINS UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRAN DERIVATIVE;

ARTICLE; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

BETULACEAE;

EID: 0025912787 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)92368-2 Document Type: Article

Times cited : (54)

References (35)

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- A typical experimental procedure is as follows: A flame-dried 10mL round-bottomed flask was charged with 295 mg (1.69 mmol) 3-bromo-2-pyrone (freshly triturated from diethyl ether), 17.0 mg of barium carbonate, 3.0 mL of anhydrous benzene, and 526 mg (5.47 mmol, 3.2 eq.) of 2-methylene-4-butanolide under argon and then refluxed for 36.5 hours. The reaction mixture was cooled, an additional 349 mg (3.63 mmol, 2.1 eq.) of the dienophile was added and refluxed for 40 hours. After cooling, the reaction mixture was diluted with 1:1 methylene chloride/ethyl acetate, filtered through a sintered glass funnel, the solvent removed by rotary evaporation, held under high vacuum to remove excess dienophile, and then passed through a plug of flash silica gel to give a pale white solid. This was recrystallized from ethyl acetate/hexane followed with purification of the supernatant by silica gel column chromatography to afford 321.2 mg (1.18 mmol, 70%) of the bicycloadduct 6 [[Truncated]]

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