Efficient condensation of carboxylic acids with alcohols catalyzed by fluorous ammonium triflates

Tetrahedron Letters

Volumn 48, Issue 17, 2007, Pages 3053-3056

  Mercs, László ^a   Pozzi, Gianluca ^a   Quici, Silvio ^a  

^a CNR   (Italy)

Author keywords

Atom economy; Dehydration; Esterification; Hydrophobic effect; Recycling

Indexed keywords

ALKANOL; AMMONIUM FLUORIDE; CARBOXYLIC ACID; ESTER; FLUORIDE; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; ESTERIFICATION; PHASE SEPARATION; POLYMERIZATION; WATER STRESS;

EID: 33947606164     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.02.117     Document Type: Article

References (31)

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30. Typical procedure: a vial fitted with a stirring bar was charged with a solution of carboxylic acid (1 mmol) and alcohol (1 mmol) in toluene (1 mL). Triflate 3 (10.8 mg, 0.01 mmol) and PDMC (1 mL) were then added. The vial was sealed with a screw cap and the biphasic reaction mixture was vigorously stirred at 80 °C for the time indicated in Table 2. After this time the mixture was cooled to rt. The upper organic layer was separated and the fluorous layer was washed with cold toluene (3 × 0.5 mL). The combined organic extracts were evaporated under reduced pressure to give the ester that was purified by column chromatography (light petroleum ether/diethyl ether) on a short silica pad if required.
31. 3), -81.1 (t, J = 10 Hz, 6F), -110.8 (t,J = 13 Hz, 4F), -120.8 (br s, 4F), -121.6 (br s, 8F), -122.2 (br s, 4F), -122.4 (br s, 4F), -126.0 (br s, 4F).