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Synlett 2016; 27(16): 2378-2383
DOI: 10.1055/s-0035-1562779
DOI: 10.1055/s-0035-1562779
letter
A Combination System of p-Toluenesulfonic Acid and Acetic Acid for the Hydration of Alkynes
Authors
Further Information
Publication History
Received: 16 April 2016
Accepted after revision: 15 June 2016
Publication Date:
15 July 2016 (online)
Abstract
A simple combination system of p-toluenesulfonic acid/acetic acid has been developed for efficient hydration of alkynes. The corresponding ketones can be obtained in good to excellent yields under mild conditions. The mechanism of the reaction was disclosed unambiguously which was a stepwise process (addition and then hydrolysis). Furthermore, this system was proved to be powerful that has the potential to be used to synthesize vinyl 4-methylbenzenesulfonates.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562779.
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- 15 General Procedures for Alkyne Hydration The corresponding alkyne (1 mmol) was added to a solution of PTSA·H2O (1 mmol, 0.190 g), AcOH (0.5 mL) in CH2Cl2 (1.0 mL). The reaction was then sealed and stirred at the indicated temperature (°C) and for the indicated amount of times (h) in Table 2. After completion, sat. aq NaHCO3 (10 mL) was added to quench the reaction and then extracted with CH2Cl2 (3 × 10 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography to give the pure product. Acetophenone (2a) Colorless liquid; yield: 114 mg (95%). 1H NMR (500 MHz, CDCl3): δ = 7.95 (d, J = 7.5 Hz, 2 H), 7.56–7.54 (m, 1 H), 7.46–7.43 (m, 2 H), 2.59 (s, 3 H). 13C NMR (125 MHz, CDCl3): δ = 198.18, 137.16, 133.12, 128.59, 128.33, 26.62.