Homologation of carboxylic acids by Arndt-Eistert reaction under ultrasonic waves

Tetrahedron Letters

Volumn 37, Issue 11, 1996, Pages 1781-1782

  Winum, Jean Yves ^a   Kamal, Merhnaz ^a   Leydet, Alain ^a   Roque, Jean Pierre ^a   Montero, Jean Louis ^a  

^a Lab Chim Biomoleculaire Associe A   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE;

ARTICLE; DRUG ACTIVATION; DRUG SYNTHESIS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; TECHNIQUE; ULTRASOUND;

EID: 0030009587     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00130-X     Document Type: Article

References (8)

1. Bachman, W.E., Struve, W.S. Organic Reactions 1942, 38-62. John Wiley and Sons, New-York, N-Y.
2. Meier, H. and Zeller, K.P. Angew. Chem. Int. Ed. 1975, 14, N°1, 32-43.
3. Wolff, L. Liebigs Ann. Chem. 1902, 325, 129.
4. Arndt, F. and Eistert, B. Ber. Deut. Chem. Ges. 1935, 68, 200.
5. Newman, S.M. and Beal, P.F. J. Am. Chem. Soc. 1950, 72, 5163-5164.
6. Mason, T.J. Chemistry with ultrasound, Elsevier, London, 1990. and references cited there in.
7. General procedure: A solution of 1g of silver benzoate in 9.1g of triethylamine was prepared and filtered to remove small amount of precipitate. The diazomethylketone (100 mg) is dissolved in 10 mL of anhydrous methanol. 1 mL of silver benzoate solution is added. The mixture was then allowed to react under sonication The rise in temperature due to the ultrasonic activation did not exceed 8°C.(Ultrasonic equipment: vibra-cell 600W, maximal power used: 360 W, reactor volume: 100 mL, sounding line diameter: 13 mm high intensity). The reaction is monitored by TLC. After filtration and concentration, the residue is purified by column chromatography (silica).
8. Links, J.; De Groot, M.S. Rec. Trav. Chim. 1953, 72, 57-61.