Pentanoic acid, 2-oxo-, 1,1-dimethylethyl ester synthesis
- Product Name:Pentanoic acid, 2-oxo-, 1,1-dimethylethyl ester
- CAS Number:88945-69-1
- Molecular formula:C9H16O3
- Molecular Weight:172.22
Yield:88945-69-1 71%
Reaction Conditions:
with pyridine;methanesulfonyl chloride in tetrahydrofuran at 0 - 20;
Steps:
General procedure for the preparation of α-ketoesters
General procedure: The α-ketoesters 2a-2e were synthesized starting from the corresponding commercially available α-ketoacids according to the literature (Yang, J.; List, B. Org. Lett. 2006, 8, 5653). Typically, the 1,2-ketoacid (10 mmol, 1.0 equiv), the corresponding alcohol (20 mmol, 2.0 equiv) and pyridine (25 mmol, 2.5 equiv) were dissolved in THF (10.0 mL) and the reaction mixture was cooled to 0 °C. Mesyl chloride (12 mmol, 1.2 equiv) was then added dropwise. The reaction was then warmed to room temperature and stirred for 30 hours. The reaction was quenched with water (20.0 mL) and extracted with diethyl ether (3 x 20.0 mL). The combined organic layers were then dried over Na2SO4, filtered and concentrated in vacuo. The resulting crude product was purified by flash column chromatography on silica gel (diethyl ether / petroleum ether = 1:10) to afford the desired 1,2-ketoester.
References:
Becerra, Diana;Raimondi, Wilfried;Dauzonne, Daniel;Constantieux, Thierry;Bonne, Damien;Rodriguez, Jean [Synthesis,2017,vol. 49,# 1,art. no. SS-2016-Z0383-OP,p. 195 - 201] Location in patent:supporting information
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