Synthesis of diethers derived from dianhydrohexitols by phase transfer catalysis under microwave

Tetrahedron Letters

Volumn 41, Issue 18, 2000, Pages 3367-3370

  Chatti, Saber ^a   Bortolussi, Michel ^a   Loupy, André ^a  

^a UNIVERSITÉ PARIS SUD   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE; HEXOSE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; HEATING; MICROWAVE RADIATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0034728831     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00416-0     Document Type: Article

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20. Typical procedure: In a pyrex cylindrical reactor adapted to the Synthewave reactor, 6.85 mmol (1 g) of D-hexitols were mixed with 20 mmol of alkyl halide, 1.4 mmol of TBAB, 20 mmol of powdered KOH (1.34 g) [containing about 15% of water] and 1 mL of solvent. The mixture was then homogenized and submitted to microwave under mechanical stirring for the adequate time. The temperature was measured by IR detection and controlled with an optical fiber throughout the reaction. It is maintained constant by modulation of the emitted power between 15 W and 300 W. The mixture was cooled down to room temperature and diluted with 40 mL of methylene chloride. The solution was filtered (KOH in excess, generated salts). The organic layer was then analyzed by GC after addition of an internal standard. In the best cases, pure products were isolated by liquid chromatography on silica gel (eluant: ethyl acetate/pentane mixtures).
21. Loupy, A.; Pardo, C. Synth. Commun. 1988, 18, 1275.