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Synlett 2019; 30(15): 1820-1824
DOI: 10.1055/s-0039-1690157
DOI: 10.1055/s-0039-1690157
letter
Synthesis of Esters from Stable and Convenient Sulfoxonium Precursors under Catalyst- and Additive-Free Conditions
Y.Y. thanks the China Scholarship Council for financial support.Weitere Informationen
Publikationsverlauf
Received: 16. Juli 2019
Accepted after revision: 25. Juli 2019
Publikationsdatum:
13. August 2019 (online)
Abstract
A convenient and efficient procedure for the construction of esters from stable sulfoxonium ylides and alcohols has been developed. This protocol presents a broad substrate scope and good yields of the desired esters can be isolated. Notably, no catalyst, oxidant, base or any other additive is required.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690157.
- Supporting Information
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References and Notes
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- 12 General Procedure: Sulfoxonium ylide 1 (0.2 mmol) was added to neat alcohol (0.5 mL) or to alcohol/tBuOH (2:3, 0.5 mL), and the solution was stirred in a 20 mL sealed tube under an atmosphere of air at 120 °C for 40 h. After cooling the mixture to room temperature, the solvent was evaporated under vacuum, and the crude product was purified by column chromatography (silica gel, pentane/EtOAc) to obtain the pure product. Butyl benzoate (2a): 1H NMR (300 MHz, CDCl3): δ = 8.20–7.85 (m, 2 H), 7.54–7.45 (m, 1 H), 7.43–7.32 (m, 2 H), 4.30 (t, J = 6.6 Hz, 2 H), 1.87–1.58 (m, 2 H), 1.58–1.26 (m, 2 H), 0.96 (t, J = 7.4 Hz, 3 H). 13C NMR (75 MHz, CDCl3): δ = 166.5, 132.7, 130.5, 129.5, 128.2, 64.7, 30.8, 19.2, 13.7.