Monoalkylation of dihydroxycoumarins via Mitsunobu dehydroalkylation under high intensity ultrasound. The synthesis of ferujol

Tetrahedron Letters

Volumn 44, Issue 46, 2003, Pages 8383-8386

  Cravotto, Giancarlo ^a   Chimichi, Stefano ^b   Robaldo, Bruna ^a   Boccalini, Marco ^b  

^a UNIVERSITY OF TURIN   (Italy)

^b UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Dihydroxycoumarins monoalkylation; Ferujol synthesis; High intensity ultrasound; Mitsunobu dehydroalkylation

Indexed keywords

ALCOHOL DERIVATIVE; DAPHNETIN; ESCULETIN; FERUJOL; PHYTOESTROGEN; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; DRUG SYNTHESIS; MAGNETISM; MITSUNOBU REACTION; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; ULTRASOUND;

EID: 0141887607     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.114     Document Type: Article

References (33)

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23. General conditions for the Mitsunobu reaction. A solution in anhydrous THF containing triphenylphosphine (1 equiv.), the alcohol (1 equiv.) and the dihydroxycoumarin was sonicated at 10°C under an argon atmosphere (18.0 kHz, 380 W). Diisopropyl azodicarboxylate (DIAD) (1 equiv.) was added dropwise over 5 min. The orange-red colour of DIAD immediately disappeared and a weakly exothermic reaction occurred. The mixture was sonicated for 35-55 min at 20°C. When the reaction was complete, as indicated by TLC (eluant: n-hexane-ethyl acetate), the mixture was evaporated. The residue was diluted with hexane-ether 3:1, v/v, filtered through a thin pad of Celite® to remove the precipitate of triphenylphosphine oxide and concentrated under reduced pressure. Finally, the products were purified by flash silica gel column chromatography or by preparative HPLC. All the reactions were carried out under nitrogen in a Teflon tube (thickness 1 mm, diameter 35 mm, volume 40 mL) inserted in the thermostatted reactor.
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