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Synlett 2015; 26(14): 2006-2008
DOI: 10.1055/s-0034-1381117
DOI: 10.1055/s-0034-1381117
letter
Ultrasound-Assisted Methyl Esterification of Carboxylic Acids Catalyzed by Polymer-Supported Triphenylphosphine
Further Information
Publication History
Received: 16 April 2015
Accepted after revision: 09 June 2015
Publication Date:
09 July 2015 (online)
Abstract
A convenient and efficient sonochemical method for methyl esterification of carboxylic acids catalyzed by polymer-supported triphenylphosphine (PS-Ph3P) is reported. In the presence of 1:0.1:2 molar ratio of 2,4,6-trichloro-1,3,5-triazine/PS-Ph3P/Na2CO3, methyl esters of various carboxylic acids bearing reactive hydroxyl groups as well as acid- or base-labile functionalities could be rapidly prepared (within 10–20 min) in good to excellent yields without necessity to pre-activate the acids. Using the polymer-bound phosphine also allows easy isolation of the products which, in most of the cases, were obtained in high purities without column chromatography.
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- 19 General Procedure The carboxylic acid (0.271 mmol), TCT (0.050 g, 0.271 mmol), PS-Ph3P (0.009 g, 0.027 mmol, loading 3.0 mmol/g), and Na2CO3 (0.057 g, 0.542 mmol) were added to MeOH (0.5 mL). Then the mixture was sonicated in an ultrasonic bath (Elmasonic S 30H) at 50 °C for the specified time. After completion, the crude mixture was filtered through a short pad of silica to obtain the product after solvent evaporation. Whenever necessary, the product was further purified by flash chromatography.
- 20 Methyl Cinnamate (Table 1 Entry 13) Colorless oil (0.036 g, 82% yield); Rf = 0.48 (5% EtOAc–hexane). 1H NMR (400 MHz, CDCl3): δ = 7.69 (d, J = 16.0 Hz, 1 H), 7.53–7.50 (m, 2 H), 7.38–7.36 (m, 3 H), 6.44 (dd, J = 16.0, 0.8 Hz, 1 H), 3.80 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ = 167.4, 144.9, 134.4, 130.3, 128.9, 128.1, 117.8, 51.7. LRMS (EI): m/z (rel. intensity) = 162 (25) [M+], 131 (100), 103 (61), 77 (33).
- 21 (9H-Fluoren-9-yl)methyl (Methoxycarbonyl)glycinate (Table 1 Entry 19) Colorless oil (0.0717 g, 85% yield); Rf = 0.46 (40% EtOAc–hexane). 1H NMR (400 MHz, CDCl3): δ = 7.76 (d, J = 7.6 Hz, 2 H), 7.60 (d, J = 7.6 Hz, 2 H), 7.39 (t, J = 7.6 Hz, 2 H), 7.31 (t, J = 7.6 Hz, 2 H), 5.43 (br s, 1 H), 4.41 (d, J = 6.8 Hz, 2 H), 4.23 (t, J = 6.8 Hz, 1 H), 3.99 (d, J = 5.2 Hz, 2 H), 3.75 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ = 170.5, 156.4, 143.8, 141.3, 127.7, 127.1, 125.1, 120.0, 67.2, 52.4, 47.1, 42.7. LRMS (EI): m/z (rel. intensity) = 311 (3) [M+], 178 (100), 165 (28).
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